Phenol → 3,5-Dichloro-4-(phenoxymethyl)-2-pyridinamine

Participants

Reaction Conditions

Reaction Steps

Sodium phenoxide was prepared by the reaction of phenol (250 mg, 2.7 mmol) and sodium hydride (60% in oil, 106 mg, 2.7 mmol) in dry THF (15 ml) at RT. The solvent was removed in vacuo and replaced with dry DMF (10 ml), 3,5-dichloro-4-(chloromethyl)-2-pyridinamine (300 mg, 1.2 mmol) was added and the mixture heated to 60° C. for 2.5 h. After cooling to RT, the reaction mixture was diluted with water (15 ml) and extracted with diethyl ether (4×15 ml)). The combined ethereal extracts were washed with water and saturated brine, dried over MgSO4, then concentrated to a solid. This was crystallised from methylene chloride and hexane to give the title compound as a white solid (219 mg+2nd crop of 45 mg, 1.0 mmol):

Provenance & Evidence