Category: 5332-26-3

Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C9H6BrNO2

General procedure: S-alkylation of the products was achieved by following a modified method [38]. The oxadiazoles (6a, 6b, 13) (0.02, mol) and K2CO3 (0.022, mol) were stirred in 10mL of acetone for 20 mints followed by the addition of alkyl bromides 7a-c and 7d-m (0.022, mol). The reaction mixture was stirred for 4-6h at room temperature. The reaction mixture was concentrated under vacuum and crude solid gained was recrystallized from methanol to get pure products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-26-3, its application will become more common.

Reference:
Article; Batool, Farwa; Hamdani, Syeda Shamila; Hameed, Shahid; Khan, Bilal Ahmad; Mughal, Ehsan Ullah; Saeed, Muhammad; Saleem, Hafiza Nosheen; Bioorganic Chemistry; vol. 96; (2020);,
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Synthetic Route of 5332-26-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Bromomethylphtalimide (85 mg, 0.35 mmol), sodium iodide (53 mg, 0.56 mmol) and cesium carbonate (177 mg, 0.54 mmol) were added to a solution of DO3AtBu under argon atmosphere (172 mg, 0.33 mmol) in freshly distilled acetonitrile (5 mL). The suspension was heated to reflux for 24 h, before being filtered at room temperature. The yellow filtrate was evaporated under reduced pressure and 10 mL chloroform was added in order to precipitate residual inorganic impurities. Evaporation of the solvent and addition of 20 mL of ether led to precipitation of a yellow powder corresponding to the sodium adduct C35H55N5O8.NaI.H2O (191 mg, 67% yield). 1H NMR (CDCl3) d: 7.82-7.71 (m, 4H), 4.66 (s, 2H), 3.27-2,34 (broad signals overlapping, 22H), 1.48-1,40 (two signals overlapping, 27H); 13C NMR (CDCl3) d: 173.91, 173.30, 169.70, 134.58, 131.69, 123.59, 83.03, 82.73, 57.62, 56.48, 55.69, 53.55, 51.77, 51.15, 48.34, 28.06, 27.88. Anal. Calcd for C35H55N5O8.NaI.H2O: C, 49.94; H, 6.83; N, 8.32. Found: C, 50.13; H, 6.67; N, 8.49.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Bromomethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; De La Reberdiere, Arnaud; Lachaud, Fabien; Chuburu, Francoise; Cadiou, Cyril; Lemercier, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6115 – 6118,4;,
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Indoline | C8H9N – PubChem

Application of 5332-26-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5332-26-3, Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 2-(Bromomethyl)isoindoline-1,3-dione

3.5 g (87 mmol) of sodium hydride are added in portions to a solution of 25 g (87 mmol) of dimethyl2- (4- ert-butoxycarbonylpiperazin-l-yl) malonate in 250 ml of tetrahydrofuran cooled to 2C. The reaction medium is stirred at ambient temperature for 30 minutes, then brought to 2C before dropwise addition of 21 g (87 mmol) of 2- (bromomethyl) isoindole-1, 3-dione in 200 ml of tetrahydrofuran . The reaction medium is stirred at ambient temperature for 20 h, treated by addition of 500 ml of water then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum.The crude product obtained is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2- (4- ert-butoxycarbonylpiperazin-l-yl) -2- (1, 3-dioxo- 1, 3-dihydro-isoindol-2-ylmethyl) malonate are obtained in the form of a white solid.

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; CHAMBON, Sandrine; CLARY, Laurence; SCHUPPLI, Marlene; WO2011/33009; (2011); A1;,
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Reference of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Weigh Intermediate LNa-3 (0.1g, 0.4984mmol) in 50mL round-bottom flask was added dimethyl formamide (15mL) was dissolved with stirring at room temperature, was added sodium bicarbonate (0.0460g, 0.5482mmol) was stirred heated to 40 after 1.5h, then slowly added dropwise bromomethyl-N- phthalimide (0.2393g, 0.9968mmol) in dimethyl formamide dropwise completed (2h), TLC monitoring, the reaction is complete, the reaction is stopped, most of the solvent was distilled off, ethyl acetate (6mL) reconstituted added washed three times (3 ¡Á 5mL), saturated brine (5mL) wash, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to dryness to give the crude product, and then with the volume fraction of 95% ethanol recrystallization, in pure LN-S-5.In various intermediate and LN-3-bromomethyl-N- phthalimide were prepared by the above process the compound LN-S-5 ~ target product LN-S-8, the results are as follows:

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Liu, Xinyong; Liu, Na; Zhan, Peng; Jia, Haiyong; (24 pag.)CN106008506; (2016); A;,
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Indoline | C8H9N – PubChem

Application of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Benzimidazole (1 mmol) and potassium hydroxide (1 mmol) were dissolved in ethyl alcohol (60 mL). The alkyl halide (1 mmol) was slowly added after the obtained reaction mixture was stirred at room temperature for 1 h. The solution was refluxed for 6 h, cooled to roomtemperature and the precipitated potassium chloride was removed by filtration. The solvent was removed by distillation. The product was then crystallized, washed several times with diethyl ether and then dried in vacuo. To a solution of 1-alkylbenzimidazole (1 mmol) in dried DMF (4 mL), alkyl halide (1 mmol) was added slowly and the reaction mixture was stirred at 80 C for 24 h under argon. After completion of the reaction, the DMF was removed by vacuum and diethyl ether (15 mL) was added to the mixture. The solid was washed with diethyl ether (2 ¡Á 15 mL) and dried under vacuum. The product was crystallized in an ethanol/diethyl ether mixture (3:1) at room temperature. The purified compounds were obtained as white or cream solids. Their structures were characterized by NMR (1H and 13C), FTIR, ESI-FTICR-MS (for 2 and 4) spectroscopic methods and elemental analysis

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Akkoc, Senem; Goek, Yetkin; Ilhan, Ilhan Oezer; Kayser, Veysel; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 81 – 88;,
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Indoline | C8H9N – PubChem

Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Diethyl (aminomethyl)phosphonate was synthesized according to literature procedure (see Kalman et a. Inorg. Chem. 2007, 46, 5260) The compound was isolated as yellow liquid 64% yield (1.082g).?H NMR (300 MHz, CDC13) 4.17-4.08 (m, 4H), 3.01 (d, J 10.3 Hz, 2H), 1.85 (bs, 2H), 1.34 (t, J 7.1 Hz, 6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; TSANTRIZOS, Youla S.; POIRIER, Judes; SEBAG, Michael; BERGHUIS, Albert; PARK, Jaeok; WIM DE SCHUTTER, Joris; WO2014/78957; (2014); A1;,
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Indoline | C8H9N – PubChem

Related Products of 5332-26-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of LiHMDS (31.3 mL, M in THF) in THF (40 mL) was added at -78C a solution of intermediate A.ii (6.50 g, 26 mmol) in THF (50 mL) over 10 min. After stirring for 1 h at -78C, a solution of N-(bromomethyl)phthalimide in THF (50 mL) was added dropwise over 10 min. The mixture was stirred at -78C for 1 h and then at rt overnight. The resulting solution was quenched with INHCl (260 mL) and extracted with DCM. The combined org. layers were washed with water, dried over MgSO4, concentrated and purified by CC (Hept/EA 1 :1). The resulting solid was triturated with EA to afford the title intermediate as a colourless solid (2.42 g, 23% yield). MS (ESI, m/z): 409.3 [M+H+].

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); A1;,
Indoline – Wikipedia,
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Electric Literature of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem