Methanol → 4-Nitro-2-(trifluoromethyl)benzaldehyde

Participants

Reaction Steps

To 4-nitro-2-(trifluoromethyl)benzonitrile (100 mg, 0.463 mmol) in toluene (3 mL) at 0° C. under argon was added DIBAL-H (0.51 mL, 1M in toluene, 0.51 mmol) and the reaction stirred for 3.75 h. MeOH and sulphuric acid were added and the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated and the residue was portioned between EtOAc (10 mL) and water (10 mL). The organic phase was dried and concentrated to give the crude product which was purified by column chromatography eluting with 0-15% EtOAc/petroleum ether to give the title compound as a yellow oil (91 mg), δH (CDCl3, 400 MHz) 10.47 (1H, s), 8.66 (1H, d), 8.56 (1H, dd), 8.33 (1H, d).

Provenance & Evidence