Triethylamine → 4-bromo-N-methoxy-N,2-dimethylbenzamide

To a solution of 4-bromo-2-methyl-benzoic acid (1.00 g, 4.65 mmol) in methylene chloride (40 mL) at room temperature, were added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.936 g, 4.88 mmol), triethylamine (1.49 mL, 1.07 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.544 g, 5.86 mmol). The mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL) and washed with 0.5 M aqueous sodium hydroxide solution (75 mL). The aqueous layer was separated, extracted with ethyl acetate (50 mL) and the organic extracts combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel gradient eluted between 0 and 50% v/v ethyl acetate in hexanes to give 4-bromo-N-methoxy-2,N-dimethyl-benzamide (886 mg, 74%).

1. washwashed with 0.5 M aqueous sodium hydroxide solution (75 mL)
2. customThe aqueous layer was separated
3. extractionextracted with ethyl acetate (50 mL)
4. washwashed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by chromatography over silica gel gradient
9. washeluted between 0 and 50% v/v ethyl acetate in hexanes

ORD record

ord-144971697efb40e7b04476e08af7e6a2

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063085B2