Chloroacetyl chloride → 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

Temperature

15 °C

To a mixture of 2-amino-4-bromophenol (50 g, 266 mmol) and NaHCO3 (67.0 g, 798 mmol) in water (200 mL) and DME (200 mL) was added 2-chloroacetyl chloride (45.1 g, 399 mmol) at 0° C. The mixture was stirred at 15° C. for 0.5 h and then stirred at 80° C. overnight. The mixture was cooled to ambient temperature and quenched with water (400 mL). The precipitate was collected by suction filtration, washed with water (200 mL) and petroleum ether (300 mL) in turn, and dried to give 6-bromo-4H-benzo[1,4]oxazin-3-one (59 g, 97%) as a gray solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.07 (d, J=8.4 Hz, 1H), 7.02 (s, 1H), 6.90 (d, J=8.4 Hz, 1H), 4.59 (s, 2H).

1. stirringstirred at 80° C. overnight
2. temperatureThe mixture was cooled to ambient temperature
3. customquenched with water (400 mL)
4. filtrationThe precipitate was collected by suction filtration
5. washwashed with water (200 mL) and petroleum ether (300 mL) in turn
6. customdried

ORD record

ord-e0211314a1564ce8b5ae7c15e01d60e4

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115151B2