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

Triethylamine (2.4 mL, 17 mmol) was added to 2-amino-4-bromophenol (2.5 g, 13 mmol) in THF (80 mL). The reaction was cooled in ice and chloroacetyl chloride (1.12 mL, 14 mmol) added portionwise. It was stirred with cooling for 10 min then allowed to warm to r.t. and stirred for a further 2 h. The reaction mixture was cooled in ice and sodium hydride (1.05 g of a 60% suspension in oil, 26 mmol) was added portionwise. The mixture was stirred with ice-bath cooling for 20 min then at r.t. for 2 h before being quenched with water (20 mL). The THF was removed in vacuo and the resulting mixture diluted with water (100 mL). The precipitate was filtered off, washed with water (3×50 mL) and dried in vacuo to yield the title compound as a beige solid (2.14 g, 70%). δH (DMSO-d6) 4.60 (2H, s), 6.92 (1H, d, J 8.5 Hz), 7.02 (1H, d, J 2.3 Hz), 7.08 (1H, dd, J 8.5, 2.3 Hz), 10.81 (1H, br s).

1. temperatureThe reaction was cooled in ice
2. temperaturewith cooling for 10 min
3. stirringstirred for a further 2 h
4. temperatureThe reaction mixture was cooled in ice
5. stirringThe mixture was stirred with ice-bath
6. temperaturecooling for 20 min
7. customat r.t. for 2 h before being quenched with water (20 mL)
8. customThe THF was removed in vacuo
9. additionthe resulting mixture diluted with water (100 mL)
10. filtrationThe precipitate was filtered off
11. washwashed with water (3×50 mL)
12. customdried in vacuo

ORDレコード

ord-181b1dc58ad645a9803fe02194e08224

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08093238B2