2-Ethylphenol → 4-Bromo-2-ethylphenol

Participants

Reaction Steps

A solution of tetrabutyl ammonium tribromide (19.7 g, 41 mmol) in CHCl3 (100 mL) was added to a stirred solution of 2-ethylphenol (5 g, 41 mmol) dissolved in CHCl3 (150 mL). The reaction mixture was stirred for 2 hrs and then quenched with 5% solution of sodium thiosulfate (150 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 (8.1 g, 98%). 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