Phenol → 4-Phenoxy-6-chloropyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of phenol (1.1 g) in dimethylformamide (20 mL) was slowly added sodium hydride (60%, 805 mg) at 0° C. After the resultant mixture was stirred at 0° C. for 30 minutes, 4,6-dichloropyrimidine (1.5 g) was added, followed by stirring at 25° C. for 1 hour and then addition of saturated aqueous ammonium chloride solution (20 mL). Then, the obtained mixture was diluted with ethyl acetate (50 mL) and washed three times with brine (30 mL each time). An organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The title compound (1.2 g) was obtained by silica gel column chromatography (ethyl acetate/n-hexane=1/10).

Provenance & Evidence