Ethyl Acetate → 4-Bromo-2-methoxy-6-methylaniline

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottom flask, 2-methoxy-6-methyl-phenylamine (4.54 g, 33.16 mmol) was dissolved in 15 mL MeOH and 5 mL acetic acid. The flask was cooled to 0° C. Bromine (1.7 mL, 33.16 mmol) in 5 mL acetic acid was added to the reaction dropwise (over 30 minutes). The reaction mixture was stirred at 0° C. for 2 hours, then was warmed up to room temperature for 1 hour. The reaction mixture was concentrated down. 1N NaOH was added to neutralize the reaction at 0° C. Ethyl acetate was added to extract the reaction mixture. The organic layer was concentrated after drying over anhydrous sodium sulfate to give a dark brown solid (5.8 g, 81%). LC-MS shows 218.0 (M+1). 1H NMR (300 MHz, CDCl3): δ 6.88 (s, 1H), 6.81 (s, 1H), 3.84 (s, 3H), 2.11 (s, 3H).

Provenance & Evidence