Cl[CH2:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8].C(N(CC)CC)C>C(O)C.[Pd]>[CH3:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8]A solution of 8.01 g (0.0262 mol based on 93.5% assay) of 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide (prepared as in example 6) and 4.0 ml (0.029 mol) of triethylamine in 60 ml of ethanol was shaken with 0.160 g of 10% Pd/C under 20-50 psi of H2 pressure at room temperature. When H2 uptake was complete (4.0 hr.), the mixture was filtered to remove catalyst and partitioned between 100 ml of methylene chloride and 50 ml of water. The organic phase, combined with a small methylene chloride wash of the aqueous phase, was washed with two 50 ml portions of water and was dried using magnesium sulfate. Solvent removal in vacuo provided 6.92 g of white 2'-methyl-6'-(trifluoromethyl)-2-chloroacetanilide assaying 92.1% for a yield of 96.7%.
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