2-Ethylphenol → 4-Bromo-2-ethylphenol

Participants

Reaction Steps

A solution of tetrabutyl ammonium tribromide (41.4 g, 86 mmol) in CHCl3 (100 mL) was added to a stirred solution of 2-ethyl phenol (10 g, 81.8 mmol) dissolved in CHCl3 (100 mL). The reaction mixture was stirred for 1 hr 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 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (0-10% EtOAc in hexanes) to give the desired product (14.3 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.5 Hz, 3H), 2.60 (q, J=7.5 Hz, 2H), 6.64 (d, J=8.5 Hz, 1H), 7.17 (dd, J=8.5, 2.5 Hz, 1H), 7.24 (d, J=2.5 Hz, 1H).

Provenance & Evidence