Phenol → 3-Nitro-2-phenoxypyridine

Participants

Reaction Conditions

Reaction Steps

3.6 g (150 mmol) of sodium hydride were added, a little at a time, to a mixture of 12 g (128 mmol) of phenol and 100 ml of dimethylformamide. After the evolution of gas had ceased, the resulting mixture was treated with 18 g (114 mmol) of 2-chloro-3-nitropyridine. After the reaction mixture had been stirred at room temperature (approximately 25° C.) for 3 hours, it was treated with water. Following extraction with tert-butyl methyl ether, washing and drying the organic phase and removal of the solvent under reduced pressure, the product crystallized out. It was purified further by stirring with tert-butyl methyl ether/n-pentane. This gave 6.6 g (27%) of the title compound. A further 3.0 g (12%) of the title compound were obtained from the mother liquor.

Provenance & Evidence