1-Phenylethanol → 2-[1-(4-Chlorophenylsulfonyl)-2-phenylpropyl]-1,4-difluorobenzene

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Reaction Steps

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (100 mg, 0.330 mmol) obtained in Example 5, and DL-1-phenylethyl alcohol (79.9 μl, 0.661 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (159 μl, 0.661 mmol). The resulting mixture was heated under reflux for 13 hours under an argon atmosphere. The reaction mixture was then concentrated. The residue thus obtained was separated and purified by flash chromatography on a silica gel column (hexane:ethyl acetate=85:15). The solids thus obtained were each washed with hexane, whereby obtained were the title Isomer 299-A (low-polarity compound) (53 mg, 0.130 mmol, 40%) as a white powder and the title Isomer 299-B (high-polarity compound) (20 mg, 0.0492 mmol, 15%) as colorless columnar crystals.

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