Tetrahydrofuran → 3-Chloro-4-(trifluoromethyl)benzaldehyde

Participants

Reaction Steps

Diisobutylaluminum hydride (1.0 M in toluene, 28 mL, 28 mmol) was added slowly via syringe to a solution of 3-chloro-4-(trifluoromethyl)benzonitrile (3.79 g, 18.4 mmol) in THF (50 mL) at 0° C. The reaction was allowed to proceed for 2 hr, then warmed to ambient temperature and stirred an additional 2 hr. The reaction was then cooled to 0° C., and quenched with 3 M aq HCl (75 mL). The mixture was allowed to warm to ambient temperature, and stirred vigorously for 1.5 hr. The mixture was then transferred to a separatory funnel and diluted with Et2O. The separated organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 15% EtOAc/hexanes eluant; SF40-150 g column) yielded 2.84 g (74%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.21 (s, 1H), 8.12 (d, J=8.1, 1H), 8.07-8.02 (m, 1H).

Provenance & Evidence