3,4-Dimethylphenol → 2-Bromo-4,5-dimethylphenol

Participants

Reaction Steps

A mixture of 3,4-dimethylphenol (2 g, 16.37 mmol) in DCM (10 mL) at −78° C. was added bromine (0.843 mL, 16.37 mmol) dropwise and the reaction was stirred for 1 h at this temperature. Sat. sodium sulfite solution was added and it was then stirred 5 min at rt and then extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain 2 g oil. It was then purified with 5% EtOAc/hexane to isolate 800 mg (24%) of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 6.84 (s, 1H), 5.33-5.23 (m, 1H), 2.20 (s, 3H), 2.19 (s, 3H).

Provenance & Evidence