Bromine → 2-Bromo-4-ethylphenol

Participants

Reaction Steps

Bromine (11.6 mL, 0.23 mol) was added slowly to a cooled 0° C. of 4-ethylphenol (25 g, 0.21 mol) dissolved in CH2Cl2 (125 mL). After the addition was complete the reaction mixture was stirred for 5 mins and then quenched with 1N NaOH. The reaction mixture was diluted with H2O and the layers separated. The organic layer was concentrated to an orange oil. Purification by flash column chromatography (0% to 5% EtOAc in hexanes) gave the title compound as a clear oil (42 g, 98%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3H), 2.58 (q, J=7.5 Hz, 2H), 5.36 (s, 1H), 6.93 (d, J=8.3 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 7.28 (s, 1H).

Provenance & Evidence