Ammonium Chloride → 2-Chloro-5-(2,3-difluorobenzoyl)pyridine

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Reaction Steps

To a solution of 1-bromo-2,3-difluorobenzene (0.114 g, 0.746 mmol) in 3 ml of dry THF was added, at −78° C., n-butyl lithium (1.6 M in hexane, 0.47 ml, 0.749 mmol). The reaction mixture was stirred at this temperature for 1 hour. A solution of 6-chloro-N-methoxy-N-methyl-nicotinamide (0.13 g, 0.68 mmol) in 5 ml of THF was added and the reaction mixture was allowed to warm to RT and stir for 6 hours. Saturated NH4Cl was added and the mixture was extracted with CH2Cl2 (3×10 ml). The organic layers were combined, washed with brine, and dried over NaSO4. The solvents were removed in vacuo and the residue was purified by column chromatography (Hex/AcOEt 9:1) to give 130 mg (77%) of an oily product. IR, NMR.

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