[CH3:1][O:2][C:3]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:6]([C:7]#N)=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16].[OH2:19]>C(O)(=O)C.N1C=CC=CC=1.[Ni]>[CH3:1][O:2][C:3]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:6]([CH:7]=[O:19])=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16]Into a 100-mL round-bottom flask, was placed 4-methoxy-3,5-bis(trifluoromethyl)benzonitrile (868 mg, 3.23 mmol, 1.00 equiv), a solution of NaH2PO2.H2O in water (10.0 mL), acetic acid (10.0 mL), pyridine (20.0 mL), Raney-Ni (0.9 g). The resulting solution was stirred for 3 h at 45° C. in an oil bath. The reaction progress was monitored by GCMS. The solids were filtered out. 20.0 mL EtOAc and 20.0 mL H2O were added into the mixture. The organic phase was washed by H2O with 2*20 mL and dried over Na2SO4. The solvent was removed and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). This resulted in 0.43 g (49%) of 4-methoxy-3,5-bis(trifluoromethyl)benzaldehyde as yellow oil. Mass spectrum (GC, m/z): Calcd. for C10H6F6O2, 272.0 (M). found 272.0.
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