[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[Cl:15][C:16]([Cl:20])([Cl:19])[C:17]#[N:18].CC(C)=O.CCOC(C)=O>CCOCC.CCOC(C)=O>[Cl:15][C:16]([Cl:20])([Cl:19])[C:17](=[NH:18])[O:14][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=1)[CH:11]([CH3:12])[CH3:13]Sodium Hydride (60%, 0.87 mmol) was suspended in Et2O (9 mL) and a solution of 1-(4-bromophenyl)-2-methylpropan-1-ol of step 1 (8.7 mmol, 2.0 g) in Et2O (6 mL) was added. The mixture was stirred at r.t. for 0.25 h. The mixture was cooled to 0° C. Trichloroacetonitrile (11 mmol) was added. The mixture was allowed to warmed to r.t. over 1 h. The mixture was diluted with EtOAc and washed with NaHCO3. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography (10% Acetone/EtOAc) gave the title compound.
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