Triethylamine → 2-fluoro-N-methoxy-N-methylbenzamide

Triethylamine (5.32 mL, 37.84 mmol) was added dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (2.768 g, 28.38 mmol) in anhydrous dichloromethane (45 mL) at 0° C. After stirring for 10 min, 2-fluorobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2×60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.116, 17 mmol) in a 90% yield.

1. customwas returned to room temperature
2. stirringstirred for 5 h
3. customThe reaction mixture was quenched with water (60 mL)
4. extractionthe products were extracted with dichloromethane (2×60 mL)
5. washThe combined organic phases were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was removed under reduced pressure
8. customPurification

ORD record

ord-cd72c5ba04a54cd0960b9aa86f026291

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877967B2