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

Temperature

5 °C

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-chlorobutyrylchloride (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 title compound as a yellow crystalline solid (10.24 g, 74%).

1. temperatureAfter 10 mins the mixture was warmed to 25° C.
2. stirringstirred for 4 hours
3. waitleft
4. waitto stand overnight
5. stirringthe mixture stirred for 30 mins
6. dry with materialthe combined extracts dried over Na2SO4
7. customThe solvent was evaporated in vacuo

ORD record

ord-e97560178fc6448283dd273e83992527

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143762