[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.Cl>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[CH:11][CH:12]=1)#[N:15]Hydroquinone (18 g, 163.5 mmol), 4-fluorobenzonitrile (10 g, 81.75 mmol) and potassium carbonate (23 g, 163.5 mmol) were heated to 150° C. in dimethylformamide (40 mL) for 6 hours. The cooled mixture was diluted with water and 1 N hydrochloric acid and extracted with ethyl acetate. The separated organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was chromatographed yielding 8 g of the title compound. MS (m/z, APCI): 210 [M−H]−.
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