Potassium Phosphate, Dibasic → 2-(2,4-Dichlorophenyl)-4-methyl-3-nitropyridine

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Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-methyl-3-nitropyridine (28; 1.08 g, 6.24 mmol), 2,4-dichlorophenyl boronic acid (1.26 g, 6.62 mmol), (Ph3P)4Pd(0) (0.405 g, 0.350 mmol), 40 mL of DMF, and 20 mL of a 2 M aqueous K2HPO4 solution was stirred at 70° C. for 40 h. The mixture was partitioned between 200 mL of diethyl ether and 200 mL of water. The organic layer was sequentially washed with 200 mL of water and 200 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a yellow oil mixed with white solid. Column chromatography (0→20% EtOAc/hexanes) afforded slightly impure 2-(2,4-dichloro-phenyl)4-methyl-3-nitro-pyridine (29; 1.19 g; 68%) as a yellow oil that was used without further purification.

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