[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl.C1C[O:32]CC1>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:32]To a solution of 2-bromo-4-hydroxy-benzonitrile (Intermediate 7, 2000 mg, 10.1 mmol) in DCM (50 mL) and THF (10 mL), at 0° C., diisobutylaluminum hydride 1M in toluene (20.2 ml, 20.2 mmol) was slowly added (10 min) and the reaction mixture was stirred at the same temperature for 1 hour. Then 40 ml of HCl 2M were added and the reaction mixture was warmed at 40° C. for 30 minutes. After cooling ethyl acetate (100 ml) was added and two phases were separated. The organic layer was washed with brine (3×100 ml) dried over sodium sulphate and concentrated under vacuum to give the title compound (1950 mg) which was used in the next step without further purification.
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