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Intermediate 502,4-Difluoro-6-(methyloxy)benzonitrile and 2,6-difluoro-4-(methyloxy)benzonitrile; A solution of 2,4,6-trifluorobenzonitrile (10 g, 63.7 mmol) in methanol (30 mL) was treated dropwise at 0 C. with 30% sodium methoxide solution in methanol (12.13 mL, 63.7 mmol). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated in vacuo and the crude solid obtained was partitioned between water (100 mL) and EtOAc (100 mL). The organic layer was separated and the aqueous one was further extracted with EtOAc (100 mL). The combined organic solutions were washed with water (100 mL) and brine (100 mL), dried through an hydrophobic frit, and concentrated under reduced pressure. The sample was loaded in cyclohexane and dichloromethane (1:1) to a 750 g silica cartridge, and purified by chromatography on Flashmaster II eluting with 0-100% methyl tert-butyl ether-cyclohexane over 40 min. The appropriate fractions were combined and evaporated in vacuo to give a mixture of the expected product (2,4-difluoro-6-(methyloxy)benzonitrile) and its regioisomer (2,6-difluoro-4-(methyloxy)benzonitrile) (1:1) LCMS (System A) RT=0.92 min, 0.95 min, ES+ve m/z 170 (M+H)+.
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