Hydroquinone → 4-(2-Bromoethoxy)phenol

Participants

Reaction Steps

To a solution of hydroquinone (1.0 g, 9 mmol) in MeOH (15 mL), KOH (1.02 g, 9 mmol) was added and stirred at room temperature for 30 minutes under argon. 1,2-dibromoethane (0.98 mL, 11.3 mmol) was added dropwise over 10 min. After the addition was complete, the mixture was refluxed for 12 hours. The reaction mixture was concentrated and was then quenched with water (50 mL) and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layer was washed with water, brine, and dried over Na2SO4. The solvent was evaporated to give a colorless oil, which was purified by column chromatography to isolate the intermediate 5a as a white solid (0.39 g, 1.79 mmol, 20% yield). 1H NMR (CDCl3, 400 MHz) δ 6.78-6.85 (m, 4H), 4.53 (s, 1H), 4.26 (t, J=6.4 Hz, 2H), 3.63 (t, J=6.4 Hz, 2H).

Provenance & Evidence