[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][OH:15])=[CH:6][CH:7]=14′-Chloro-biphenyl-2-carbaldehyde (6.50 g, 30.0 mmol) was dissolved in CH2Cl2 (75 mL) and methanol (75 mL). The solution was cooled to 0° C. in an ice bath, and then sodium borohydride (1.36 g, 36.0 mmol) was added slowly portionwise. The reaction was allowed to warm gradually to room temperature and stir for 16 hours. The reaction was quenched by addition of 2M NaOH, and the organics were extracted with CH2Cl2 (3×75 mL). The combined organic layers were dried over MgSO4 and concentrated to afford (4′-chloro-biphenyl-2-yl)-methanol (6.42 g, 98% yield), which was carried on to the next step without further purification. MS (ES1) m/e (M−H)−: 217.4
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