C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[CH3:21])=O.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:21][C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[CH2:3][OH:2]A solution of 3-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (1.993 g, 6.773 mmol) in CH2Cl2 (34 mL) at 0° C. is treated with 1.0 M diisobutylaluminum hydride in toluene (DIBAL, 14.3 mL) dropwise over 3 min. time and stirred for 3.5 h. The reaction mixture is quenched with MeOH (5.0 mL), treated with 1M tartaric acid (50 mL), and stirred overnight. The organic layer is separated. The aqueous layer is extracted with CH2Cl2 (1×50 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. to provide (3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (1.616 g, 90%) as a white solid.
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