Pyridine → 4-Bromo-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

Pyridine (4.40 mL, 54.2 mmol) was added dropwise to N,O-dimethylhydroxylamine hydrochloride (3.44 g, 35.2 mmol) dissolved in CH2Cl2 (100 mL) at RT. The reaction mixture was stirred for 30 min, and 4-bromobenzoyl chloride (5.95 g, 27.1 mmol) dissolved in CH2Cl2 (50 mL) was added dropwise. The mixture was stirred for 24 h and the volatiles were removed under reduced pressure. Water (200 mL) was added and the mixture was extracted with EtOAc (3×200 mL). The combined extracts were washed successively with 5% aqueous HCl (200 mL), 5% aqueous NaHCO3 (200 mL), water (200 mL), and brine (200 mL). The mixture was dried over MgSO4 and concentrated to afford 6.35 g (74%) of 80 as a colorless oil which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 3.35 (s, 3H), 3.53 (s, 3H), 7.54 (d, J=8.6 Hz, 2H), 7.58 (d, J=8.6 Hz, 2H).

Provenance & Evidence