[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.ClCCl.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#N.[Al+3].[Cl-].[Cl-].[Cl-].[OH2:30]>ClC1C=CC=CC=1>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:21]([C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([F:17])[CH:19]=1)=[O:30]To a 0° C. solution of para-anisidine (8.13 g, 66.0 mmol) in 25 mL of chlorobenzene was added dropwise a solution of BCl3 in dichloromethane (74.3 mL of 1 M, 74.3 mmol). The mixture was stirred at room temperature for one hour, then transferred slowly via syringe to solution of 3-fluorobenzonitrile (4.00 g, 33.0 mmol) and AlCl3 (5.06 g, 37.9 mmol) in 50 mL of chlorobenzene at 60° C. After the addition was complete, the reaction was stirred at 70° C. for 3 hours, then cooled to room temperature and stirred overnight. Water was added (125 mL), and the mixture stirred at 85 degrees for 6 hours. After cooling to room temperature, the mixture was poured into water, and the organic layer was extracted with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chomatography through SiO2 (50-100% CH2Cl2/hexane) to provide the titled product (1.83 g, 23% yield) as a red oil. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C14H13FNO2 (M+H+): 246.0929. Found 246.0925.
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