4-Bromophenol → 1-Bromo-4-[(2-methylprop-2-en-1-yl)oxy]benzene

Participants

Reaction Steps

To a solution of 4-bromo phenol (7.0 g, 40.40 mmol) in acetone (165 mL) was added K2CO3 (27.8 g, 202 mmol) followed by 3-bromo-2-methylprop-1-ene (4.9 mL, 44.5 mmol). The mixture was stirred at reflux temperature for 16 h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (200 mL), washed with H2O (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound (6) (8.0 g, 93%) as a colorless liquid. 1H NMR (CDCl3, 400 MHz) δ 7.37 (d, J=9.2 Hz, 2H), 6.81 (d, J=9.2 Hz, 2H), 5.08 (s, 1H), 5.00 (s, 1H), 4.41 (s, 2H), 1.83 (s, 3H); MS (ESI, M+H+) C10H12BrO, calcd. 227.1. found 227.0, 229.0.

Provenance & Evidence