Reference 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: After the compound 1o (700 mg, 1.68 mmol) was dissolved in dichloromethane (15 mL), potassium hydroxide (278 mg, 4.22 mmol) and tetrabutylammonium bromide (60 mg) were added thereto, and iodomethyl (0.525 mL, 8.435 mmol) was slowly added thereto at room temperature. This solution was stirred for 10 hours at 25 C. Cooling water was added to the reaction material, and the result was adjusted to pH 5 to 6 using a 2N aqueous hydrochloric acid solution. After the organic layer was separated and taken, the aqueous layer was extracted once with dichloromethane, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated using silica gel column chromatography (normal-hexane/ethyl acetate=4/1) to give a pure target compound 1z (574 mg, 79%). Step 1: Preparation of methyl 2-tert-butoxy-2-(4-(4-chlorophenyl)-1-((1,3-dioxoisoindolin-2-yl)methyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (19a) A target compound 19a (780 mg, 94%) was obtained by reacting the compound 1o (600 mg, 1.446 mmol) in the same manner as in Step 1 of Example 1, except that N-(bromomethyl)phthalimide (787 mg, 3.0 equivalents) and potassium hydroxide (400 mg, 5 equivalents) were used instead of iodomethyl and the stirring was carried out for 7 hours at 20 C. 1H-NMR (300 MHz, CDCl3) delta 0.98 (s, 9H), 1.46 (s, 3H), 2.45 (s, 3H), 2.65 (s, 3H), 3.63 (s, 3H), 5.04 (s, 1H), 6.08 (AB-q, 2H), 7.24 (m, 2H), 7.37 (m, 2H), 7.73 (m, 2H), 7.68 (m, 2H); MS (EI, m/e)=573 (M+).
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:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; US2014/249162; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem