Methyl iodide → 5-Bromo-1,3-dichloro-2-methoxybenzene

Participants

Reaction Steps

A mixture of 4-bromo-2,6-dichlorophenol (10 g, 41.67 mmol), K2CO3 (11.5 g, 83.3 mmol) and CH3I (8.88 g, 62.5 mmol) in DMF (100 mL) was stirred at rt for 16 h. TLC (EtOAc/petroleum ether=1:2) indicated complete consumption of 4-bromo-2,6-dichlorophenol. The reaction mixture was poured into water (300 mL). The aqueous phase was extracted with EtOAc (2×100 mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated in vacuo to give crude 5-bromo-1,3-dichloro-2-methoxybenzene, which was purified by column chromatography (silica gel, EtOAc/petroleum ether=1:5) to yield the ether product (9 g, yield 84.9%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.45 (s, H), 3.91 (s, 3H) ppm.

Provenance & Evidence