C(O[C:9]1[C:14](C=O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1C=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.C[Mg][Br:25].[Cl-].[NH4+:27]>O1CCCC1>[Br:25][C:14]1[CH:9]=[C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:27]=2)[CH:11]=[CH:12][CH:13]=1A solution of 2-(benzyloxy)biphenyl-3-carbaldehyde (5.55 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) was stirred under nitrogen on an water bath at room temperature and 3M methyl magnesium bromide in tetrahydrofuran (10 mL, 30 mmol, 1.5 equiv.) was added. Stirring was continued at room temperature for 40 min. The reaction mixture was poured onto saturated ammonium chloride (200 mL) and extracted with ethyl acetate (2×200 mL). The organic extract was washed with water (100 mL), dried over sodium sulfate and stripped to afford pure 1 (6 g, 98%).
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