[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]Cl)[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][S:12]([CH3:11])(=[O:14])=[O:13])[C:5]([Cl:8])=[N:6][CH:7]=1A mixture of 5-bromo-2-chloro-3-(chloromethyl)pyridine (124 mg, 0.52 mmol) and sodium methanesulfinate (52 mg, 0.52 mmol) in dioxane (1.4 mL) and water (1.4 mL) was heated to 110° C. in a microwave reactor for 15 min. After cooling to rt, water was added to the reaction mixture which was subsequently extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 5-bromo-2-chloro-3-(methylsulfonylmethyl)pyridine (140 mg, 0.49 mmol, 94% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.63 (d, 1H), 8.21 (d, 1H), 4.70 (s, 2H), 3.10 (s, 3H); MS (EI) for C7H7BrClNO2S: 284, 286, 288 (Br+Cl isotopes, MH+).
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