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

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Reaction Steps

A mixture of 4-bromo-2-methoxyphenol (5 g, 24.63 mmol), NaH2PO4 monohydrate (3.23 g, 23.40 mmol) and 2,2-dimethyloxirane (3.02 g, 41.9 mmol) in MeCN (90 ml) and H2O (10.00 ml) was stirred at 150° C. in a steel bomb for 4 hours. After cooling to RT, the mixture was diluted with a solution of saturated NaHCO3 (80 ml) and extracted with EtOAc (80 ml). The EtOAc extracts were dried over Na2SO4 and concentrated. The crude product was purified by ISCO chromatography on a silica gel column (120 g) employing a 10 min gradient ranging from hexane to 30% EtOAc/hexane to elute 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol (6.25 g, 22.72 mmol, 92% yield) as clear oil. LC MS at t=2.24 min. (m+Na=297) Phenomenex S5 C18 4.6×30 mm column/water-MeOH-TFA 90:10:0.1 to 10:90:0.1 gradient over 2 min at 5 mL/min with 1 min hold at the end of the gradient. 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 6H), 3.79 (s, 2H), 3.84 (s, 3H), 6.77 (d, J=8.31 Hz, 2H), 7.01 (s, 1H), 7.26 (s, 1H).

Provenance & Evidence