4-Chloro-2-methylphenol → 2-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-nitropyridine

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Reaction Steps

Sodium hydride (60% in mineral oil, 1.08 g, 27 mmol) was washed 3× with hexanes then a solution of 4-chloro-2-methylphenol (3.50 g, 24.5 mmol) dissolved in tetrahydrofuran (40 mL) was added. The solution was stirred for 20 minutes then 2-chloro-3-methyl-5-nitropyridine (4.02 g, 23.3 mmol) was added and the reaction mixture was heated to reflux for 3 hours. After cooling, the mixture was concentrated in vacuo then dissolved in ethyl acetate and washed with water, 3× with saturated NaHCO3− and saturated NaCl then dried over Na2SO4 and concentrated in vacuo.

Provenance & Evidence