[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.CO[Na].[H][H]>CO>[C:6]([O:8][CH3:9])(=[O:7])[C:5]1[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1.[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1To a 100 ml stainless steel autoclave, 6.0 mg (0.01 mmol) of complex 1 and 430 mg (2 mmol) of methyl p-bromobenzoate were added, and the autoclave was purged with nitrogen. Then, 0.5 ml (0.5 mmol) of 1 N MeONa and 1.5 ml of methanol were added thereto. Subsequently, hydrogen was introduced to a pressure of 5.0 MPa, followed by stirring at 80° C. for 16 hours. After cooling to room temperature, the reaction product was analyzed by GC. Merely dibromination of 31% of the substrate occurred which resulted in conversion to methyl benzoate (debrominated product), and p-bromobenzyl alcohol was not detected.
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