2-Ethyl-5-methoxyphenol → 4-Bromo-5-methoxy-2-ethyl-phenol

Participants

Reaction Steps

A solution of tetrabutyl ammonium tribromide (38.10 g, 79 mmol) in CHCl3 (100 mL) was added to a stirred solution of 5-methoxy-2-ethyl-phenol (12.0 g, 79 mmol) dissolved in CHCl3 (90 mL). The reaction mixture was stirred for 4 hrs and then quenched with 5% solution of sodium thiosulfate (90 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1 N HCl, brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 60% EtOAc in hexanes) gave the product as an oil (19 g). LCMS: APCI−VE=230 M/E.

Provenance & Evidence