2,4-Difluorobenzaldehyde → HCID 67257315, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-2-methoxypyridine 1 (2.10 g, 10.6 mmol) in anhydrous TBME (20 ml) at −32° C. under argon atmosphere was added n-BuLi solution (5.8 ml of 2 M solution in cyclohexane, 11.7 mmol) drop wise over 15 min under argon condition. After stirring for 1 h, 2,4-difluorobenzaldehyde (1.54 g, 10.6 mmol) was added drop wise over 15 min and the reaction mixture was stirred for 30 min under −32° C. under argon atmosphere. Reaction mixture was allowed to warm up to 0° C. and quenched with saturated NH4Cl (20 ml). The phases were separated and the aqueous layer was extracted with TBME (20 ml and 10 ml). All combined organic phases were washed with water (50 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 85:15). Yield 2.28 g (850%). 1H NMR (CDCl3, 500 MHz): δ 8.16 (s, 1H), 7.57-7.52 (m, 2H), 6.93-6.76 (m, 2H), 6.72 (d, 1H, J=9.0 Hz), 6.07 (d, 1H, J=3.5 Hz), 3.92 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ 163.9, 162.4, 159.6, 145.0, 137.2, 131.0, 128.2, 126.5, 111.5, 110.9, 103.9, 67.3, 53.6.

Provenance & Evidence