2-Ethylphenol → 4-Bromo-2-ethylphenol

Participants

Reaction Steps

A solution of tetrabutyl ammonium tribromide (39.56 g, 0.08mol) in CHCl3 (100 mL) was added to a stirred solution of 2-ethyl-phenol (10.0 g, 0.08 mol) dissolved in CHCl3 (100 mL). The reaction mixture was stirred for 2 hrs and then quenched with 5% solution of sodium thiosulfate (100 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 15% EtOAc in hexanes) gave the product as an oil (14 g.). LCMS: APCI−VE=200 M/E.

Provenance & Evidence