Hydrochloric Acid → 1-Bromo-3-methoxy-5-methylbenzene

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask, 4-bromo-2-methoxy-6-methyl-phenylamine (5.8 g, 26.84 mmol) was charged with acetic acid (49 mL) and concentrated HCl (5.6 mL). Sodium nitrite (2.19 g, 31.78 mmol) in 7 mL water was added to the mixture dropwise at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. 50% Hypophosphorous acid (56.5 mL) was added at 0° C. The reaction mixture was stirred at 0° C., and warmed up to room temperature overnight. Ethyl acetate was then added, followed by washing with saturated NaHCO3 solution. The organic layer was concentrated and purified (silica gel, 100% hexane) to give a pale liquid (5.12 g, 95%). 1H NMR (300 MHz, CDCl3): δ 6.97 (s, 1H), 6.87 (s, 1H), 6.64 (s, 1H), 3.80 (s, 3H), 2.36 (s, 3H).

Provenance & Evidence