Thionyl Chloride → 1,1'-(Chloromethylene)bis(4-fluorobenzene)

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To 5.00 g (22.7 mmol) of 4,4'-difluorobenzhydrol was added 16.5 ml (227 mmol) of thionyl chloride in the atmosphere of argon, and the mixture was stirred at room temperature for 30 minutes. To the resulting mixture was added water followed by extraction with benzene. The organic layer was successively washed with saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to column chromatography on silica gel. There was yielded 4.90 g (20.5 mmol) of 4,4'-difluorobenzhydryl chloride from the fraction eluted with benzene.

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