Sodium hydride → HCID 68266063, compound

Participants

Reaction Steps

60% Sodium hydride in oil dispersion (1.2 g, 29.88 mmol) was added portionwise over 5 mins to an ice-cooled, stirred solution of N-(3-bromo-4-fluoro-phenyl)-4-chloro-butanamide (which may be prepared as described in Description 57) (8 g, 27.16 mmol) in dry THF (150 mL) under N2. After cooling for a further 5 mins the cooling bath was removed and the mixture stirred at ambient temp for 2 hours. The reaction mixture was then treated with AcOH (1 ml) by dropwise addition. The mixture was evaporated and the residue partitioned between DCM (150 ml) and water (150 ml). The latter was re-extracted with DCM (50 ml) and the combined organic extracts dried (MgSO4) and evaporated to a white solid. The solid was dissolved in refluxing Et2O (65 ml) and the solution diluted with iso-hexane (240 ml) and left to stand for 1 hour. The crystalline solid was filtered and dried. The filtrate was concentrated to approx 50 ml volume and a 2nd crop of crystals was collected and dried. The combined mass gave N-(3-bromo-4-fluoro-phenyl)pyrrolidin-2-one (D58) (6.03 g);

Provenance & Evidence