HCID 4102537, compound → 5-bromo-2-isopropyl-2,3-dihydro-1H-isoindole

Participants

Reaction Steps

To a solution of 5-bromo-2-(1-methylethyl)-1H-isoindole-1,3(2H)-dione (Intermediate 5, 4.27 g) in tetrahydrofuran (THF) (100 mL) under nitrogen at room temperature was added 1.0M borane-tetrahydrofuran complex in THF (80 mL). The reaction mixture was heated at reflux for 48 hours. More 1.0M borane-THF complex in THF (50 mL) was added and the reaction mixture was heated at reflux for a further 24 hours. The reaction mixture was allowed to cool to room temperature. The reaction was quenched by the dropwise addition of 2N hydrochloric acid (80 mL). The reaction mixture was then heated at reflux for 1 hour. The reaction mixture was separated between ethyl acetate (300 mL) and water (50 mL). The organic phase was washed with 2N hydrochloric acid (100 mL). The combined aqueous phases were basified using 2N sodium hydroxide solution and then extracted with ethyl acetate (300 mL). This organic phase was washed with brine (100 mL) and dried over magnesium sulphate. The solvent was evaporated in vacuo to give the title compound (3.0 g) as a white solid.

Provenance & Evidence