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

Participants

Reaction Steps

To a solution of 3,4-dimethylphenol (2.48 g, 20.3 mmol, 1 equiv) in DCM (200 mL) at −78° C. (IPA/dry ice) was added dropwise bromine (1.05 mL, 20.3 mmol, 1 equiv). After 1 h, 1 N Na2SO3 was added and the cold bath was removed. After warming to ambient temperature, the DCM layer was separated, dried (Na2SO4), and concentrated in vacuo to provide the product (4.09 g, 100%) as a yellow solid. Regioselectivity>10:1, use as is. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 6.83 (s, 1H), 5.26 (s, 1H), 2.20 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence