3-Bromoaniline → N-3,3-Dimethylacryloyl-3-bromoaniline

Temperature

0 °C

To a suspension of Nail (4.15 g, 173 mmol, 60% in oil) in 50 ml of THF was cannulated a solution of 20.322 g (118 mmol) of 3-bromo-aniline in 50 ml of THF. The resulting mixture was stirred at 0° C. for 45 min and warmed to room temperature over a period of 15 min. To this solution was added through cannulation 13.123 g (173 mmol) of 3,3-dimethylacryloyl chloride. The mixture was stirred at room temperature for 24 h and thereafter slowly poured into ice water. The resulting mixture was extracted with methylene chloride (twice), dried over MgSO4 and concentrated to yield a solid. The solid was purified by recrystallization in hexane/EtOAc (2:1) to give the title compound as a light brown solid. PNMR (CDCl3) d 7.83 (1H, b), 7.30 (4H, m), 5.68 (1H, s), 2.22 (3H, s), 1.90 (3H, s).

1. temperaturewarmed to room temperature over a period of 15 min
2. stirringThe mixture was stirred at room temperature for 24 h
3. extractionThe resulting mixture was extracted with methylene chloride (twice),
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customto yield a solid
7. customThe solid was purified by recrystallization in hexane/EtOAc (2:1)

ORD record

ord-b353c11b68e64e809de5f4ce485a63b6

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739338