Trimethylsilyldiazomethane → 5-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

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Reaction Steps

To a solution of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (17.4 g, 48.1 mmol) in THF-MeOH (100 mL-30 mL) was added TMSCHN2 (31.0 mL, 62.0 mmol, 2M solution in hexanes) at room temperature. The resulting mixture was stirred for 2 hours, quenched with AcOH, and diluted with EtOAc. The organic layer was washed with water, saturated NaHCO3 (2×), and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give the crude product (18.0 g, 99%) that was used directly without further purification.

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