Ammonia → 4-BroMo-2,6-difluorobenzaMide, 96%

Temperature

-20 °C

To a stirred solution of the above benzoic acid intermediate (18 g, 76 mmol) in THF (150 mL)), at −20° C., was added triethylamine (7.6 g, 76 mmol) and ethyl chloroformate (9.8 g, 91 mmol. The reaction was stirred at −20° C. for 20 min. Then it was warmed up to room temperature and an ammonia solution (0.5 M in dioxane, 150 mL, 76 mmol) was added. The reaction was stirred at room temperature overnight. It was then concentrated, diluted with dichloromethane, washed with 1 N HCl and brine, and dried over Na2SO4. The solvent was removed to give the crude product as a solid. It was washed with dichloromethane to give 4-bromo-2,6-difluorobenzamide (9.4 g, 52.4%).

1. temperatureThen it was warmed up to room temperature
2. stirringThe reaction was stirred at room temperature overnight
3. concentrationIt was then concentrated
4. additiondiluted with dichloromethane
5. washwashed with 1 N HCl and brine
6. dry with materialdried over Na2SO4
7. customThe solvent was removed
8. customto give the crude product as a solid
9. washIt was washed with dichloromethane

ORD record

ord-90751d5a23e848e298fb8fd80a4e78cc

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329764B2