In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17702-83-9 as follows. Application In Synthesis of 2-(8-Bromooctyl)isoindoline-1,3-dione
step 1 8-(Benzoxazol-2-ylsulfanyl)-octylamine To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) andDMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by N-(8-bromooctyl)phthalimide (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20percent EtOAc/petroleum ether gradient) to afford the thioether intermediate. To this thioether intermediate (3.02 g, 7.39 mmol) in MeOH (40 mL) at room temperature was added hydrazine monohydrate (0.860 mL, 17.7 mmol) and the resulting mixture was heated to reflux. After 18 h at this temperature, the reaction was concentrated, taken up in EtOAc (300 mL), and filtered to remove insoluble materials. This phthalimide byproduct was washed with excess EtAOc, and the filtrate was washed with H2O (40 mL) and brine (40 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (1.87 g, 57percent) as an oil; 1H NMR (CDCl3) delta1.14-1.67 (m, 12H), 1.72-1.92 (m, 2H), 2.69 (t, J=9.6 Hz, 2H), 3.32 (t, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 7.38-7.47 (m, 1H), 7.54-7.66 (m, 1H); mass spectrum [(+) ESI], m/z 279(M+H)+.
According to the analysis of related databases, 17702-83-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Butera, John A.; Caufield, Craig E.; Graceffa, Russell F.; Greenfield, Alexander; Gundersen, Eric G.; Havran, Lisa Marie; Katz, Alan H.; Lennox, Joseph R.; Mayer, Scott C.; McDevitt, Robert E.; US6214877; (2001); B1;,
Indoline – Wikipedia,
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