4-Bromoaniline → 1-(4-Bromophenyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromoaniline (10 g, 58 mmol) in dry THF (150 ml), under argon was added triethylamine (6 g, 59 mmol) and 4-chlorobutyryl chloride (8.2 g 58 mmol) at 5° C. The mixture was stirred at 5° C. for 40 mins and potassium tert-butoxide (16 g, 142 mmol) added in one portion. After 10 mins the mixture was warmed to 25° C. and stirred for 4 hours, then left to stand overnight. Water (10 ml) was added and the mixture stirred for 30 mins. The mixture was diluted with ethyl acetate (200 ml) and 3% Na2CO3 (aq) (120 ml). The aqueous layer was reextracted with ethyl acetate (100 ml) and the combined extracts dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid (12 g). Chromatography on silica gel (~200 g) using 30-60% ethyl acetate/hexane gradient elution gave the tide compound as a yellow crystalline solid (10.24 g, 74%).

Provenance & Evidence