6-Bromopyridine-2-carbaldehyde → (6-Bromopyridin-2-yl)(4-fluorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of the 6-Bromo-2-pyridine carboxaldehyde (6.12 g, 32.90 mmol) in anhydrous THF (150 mL) @ −78° C. under N2 was added 4-fluorophenylmagnesium bromide (2M in diethyl ether, 17.27 mL) dropwise. The reaction was warmed to 0° C. and stirred for 1.5 hr. The reaction was quenched with saturated aqueous NH4Cl. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated to give (6-bromopyridin-2-yl)(4-fluorophenyl)methanol. 1H NMR (500 MHz, CDCl3) δ 7.50 (t, 1H, J=7.7), 7.40 (d, 1H, J=7.8), 7.38-7.32 (m, 2H), 7.10 (d, 1H, J=7.6), 7.03 (t, 2H, J=8.7), 5.73 (d, 1H, J=4.2), 4.43 (d, 1H, J=4.4), LRMS m/z (M+H) Calcd.: 282.0, found: 282.0.

Provenance & Evidence