Hydrochloric Acid → 2-Iodo-4-(trifluoromethyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of diisobutylaluminum hydride in toluene (13 mL, 13 mmol) was added slowly drop-wise to a 0° C. solution of 2-iodo-4-trifluoromethyl-benzonitrile (3.58 g, 12 mmol) in toluene (11 mL). The reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was warmed to room temperature, then stirred at room temperature for 24 hours. The reaction mixture was cooled to 0° C., then ethyl acetate (5 mL), and ethanol (5 mL) were added dropwise to the cold reaction mixture. After stirring at 0° C. for 10 minutes, the reaction mixture was concentrated to give a yellow, oily liquid. The residue was cooled to 0° C. Methylene chloride (10 mL) was added. Water (10 mL) was added slowly drop-wise, then 1.0 N aqueous HCl was added slowly drop-wise. After stirring at 0° C. for 10 minutes, concentrated HCl (1 mL) was added followed by additional methylene chloride (60 mL). The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature. Stirring at room temperature continued for 105 minutes. The mixture was poured into a separatory funnel, and the organic phase was separated, dried over Na2SO4, filtered, and concentrated to an oily, yellow solid. The crude product was purified using flash chromatography (RediSep® Flash column, 230-400 mesh, 0-3% ethyl acetate in hexanes) to give 1.44 g (40%) of 2-iodo-4-trifluoromethyl-benzaldehyde as a slightly yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 10.11 (s, 1 H), 8.20 (s, 1 H), 7.97 (d, J=8.2 Hz, 1 H), 7.73 (d, J=8.2 Hz, 1 H).

Provenance & Evidence