4-Toluenesulfonyl chloride → 2-(Chloromethyl)-6-fluoroquinoline

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6-Fluoro-2-methylquinoline N-oxide (2.70 g, 15.25 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (2.9 g, 15.21 mmol) in dichloroethane (100 mL). The reaction mixture was heated to 100° C. overnight under N2, cooled and concentrated, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4 and evaporated under reduced pressure to afford a solid. The crude solid was purified by flash chromatography (15:1 hexane/ethyl acetate) to afford 1.59 g (63%) of pure product as an off white solid.

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