Isobutylene oxide → 1-(4-Bromo-2-methoxyphenoxy)-2-methylpropan-2-ol

Participants

Reaction Steps

A mixture of 4-bromo-2-methoxyphenol (8 g, 39.4 mmol), 2,2-dimethyloxirane (14 mL, 158 mmol), potassium carbonate (4.3 g, 35.5 mmol), and sodium phosphate, monobasic (4.25 g, 35.5 mmol) in acetonitrile and water (85:15, 100 mL) was stirred in a steel bomb at 150-165° C. for 8 h. The reaction was cooled to RT, diluted with ether and EtOAc (1:1), washed with 1N NaOH, dried (Na2SO4), and concentrated. The crude was passed through a pad of silica gel using EtOAc for elution to afford the desired product 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol 7A (10 g, 36.3 mmol, 92% yield) as a brown oil. 1H NMR (400 MHz, CHLOROFORM-d) δ6.95-7.08 (2H, m), 6.77 (1H, d, J=8.28 Hz), 3.85 (3H, s), 3.79 (2H, s), 1.34 (6H, s).

Provenance & Evidence