Water → 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

Participants

Reaction Steps

To a solution of 52 (7.5 g, 30 mmol) and ZnCl2 (1 g) in THF (100 ml) was added SOCl2 (5.31 g, 45 mmol) dropwise. After 1 hr at rt, the reaction was poured into water and extracted with ether. The ether was dried, concentrated and the product was purified by column chromatography on silica gel (10% EtOAc/hex) to give 53 as an oil (5.5 g, 75%): 1H NMR(DMSO-d6) δ 7.21(d, 1 H, J=3.0 Hz), 7.08 (d, 1 H, J=3.0 Hz), 4.73 (s, 2 H), 3.78 (s, 3 H), 3.75 (s, 3 H)

Provenance & Evidence