Azobisisobutyronitrile → 1-Oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Temperature

80 °C

methyl 2-(bromomethyl)-4-cyanobenzoate. To a stirred solution of methyl 4-cyano-2-methylbenzoate (1 g, 5.7 mmol) in CCl4 (30 mL), was added NBS (1.4 g, 6.2 mmol), and catalytic AIBN. The reaction mixture was stirred for 48 h at 80° C. The reaction progress was monitored by TLC (10% EtOAc in hexanes). The reaction was cooled to room temperature and diluted with water (25 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, concentrated, and purified by column chromatography silica (60-120 mesh silica with 80-100% EtOAc in petroleum ether) as eluent to give the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3): δ 8.05 (d, J=8.0 Hz, 1H), 7.78 (s, 1H), 7.6 (d, J=8.0 Hz, 1H), 4.9 (s, 2H), 4.0 (s, 3H).

1. temperatureThe reaction was cooled to room temperature
2. customThe organic layer was separated
3. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
4. washThe combined organic layers were washed with brine (50 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. custompurified by column chromatography silica (60-120 mesh silica with 80-100% EtOAc in petroleum ether) as eluent

ORD record

ord-59cc6acfde6645a7a61e86514bdc8320

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952009B2