1-Bromo-4-phenylmethoxybenzene → (4-(Benzyloxy)phenyl)(5-bromo-2-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxybromobenzene (2.63 g, 10 mmol) in THF (50 mL) at −78° C. under nitrogen was slowly added n-butyllithium (2.5 M in hexanes, 4.4 mL, 11 mmol). The reaction was stirred for 30 minutes. 5-Bromo-2-methylbenzaldehyde (32, 1.99 g, 10 mmol) in THF (4 mL plus 1 mL rinse) was added slowly. The reaction was allowed to slowly warm to about 0° C. over 2 hours, then quenched with saturated aqueous NH4Cl, diluted with ether, washed with H2O and brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel flash chromatography (gradient 0-25% EtOAc/hexanes) to give 3.12 g (82% yield) of the title compound 33 as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.80 (d, J=2.3 Hz, 1 H), 7.36-7.47 (m, 4 H), 7.29-7.36 (m, 2 H), 7.18-7.24 (m, 2 H), 6.99 (d, J=8.1 Hz, 1 H), 6.88-6.97 (m, 2 H), 5.89 (d, J=3.5 Hz, 1 H), 5.06 (s, 2 H), 2.12 (s, 3 H), 2.06 (d, J=3.5 Hz, 1 H); MS (ES+) [M-OH]+=365, 367.

Provenance & Evidence