[C:1]([C:4]1[CH:5]=[C:6]([Cl:22])[C:7]([CH2:19][C:20]#N)=[C:8]([C:17]#N)[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.Cl.[OH2:40].[OH-:41].[Na+]>C(Cl)Cl>[Cl:22][C:6]1[C:7]([CH2:19][CH:20]=[O:41])=[C:8]([CH:17]=[O:40])[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=1To a mixture of 6-acetyl-4-chloro-3-(cyanomethyl)-3′-fluorobiphenyl-2-carbonitrile (0.167 g, 0.534 mmol) in methylene chloride (2 mL) was added 1.0 M diisobutylaluminum hydride in hexane (2.9 mL, 2.9 mmol) at −78° C. The reaction was warmed to room temperature over 2 hours with stirring. Hydrogen chloride (5.0 M) in water (10 mL, 50 mmol) was added slowly and stirring was continued for 1 hour. Aqueous NaOH was used to render the solution alkaline, and the resulting mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to dryness. The residue was used in the next step. LCMS calculated for C17H12ClFO2 (M-18)+: m/z=302.1; Found: 302.1
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