4-(Difluoromethyl)benzenemethanol → 4-(Difluoromethyl)benzaldehyde
Reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][CH:13]([F:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1>C(Cl)Cl>[F:12][CH:13]([F:22])[C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[CH:18][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Solid pyridinium chlorochromate (8.22 g, 38.1 mmol) was added slowly to a mixture of Example 38B (4.02 g, 25.4 mmol) and celite filter aid (8.5 g) in CH2Cl2 (125 mL) at ambient temperature. The reaction was allowed to proceed for 30 min, and then filtered. The filtrate was concentrated in vacuo to give a black oil. Flash chromatography (Analogix® Intelliflash 280™; 15% EtOAc/hexanes eluant; SF40-115 g column) yielded 3.68 g (93%) of the title compound as a colorless oil. 1HNMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.08-8.02 (m, 2H), 7.84-7.76 (m, 2H), 7.18 (t, J=55.5, 1H).