Phenol → HCID 59007102, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyl magnesium chloride (2.0 M in THF, 2.25 ml, 45 mmol) was added to a stirred solution of n-butyl lithium (1.6 M in hexanes, 5.56 ml, 8.9 mmol) at 0° C. under argon. After 10 minutes at 0° C. the mixture was cooled to −10° C. A solution of 2,6-dibromopyridine (3.0 g, 12.7 mmol) in toluene (35 ml) was added over 10 minutes and the mixture was stirred at −10° for 2 hours. After cooling to −40° C., sulfur dioxide gas was bubbled into the mixture for 5 minutes and the reaction was stirred at −40° C. for 30 minutes. Sulfuryl chloride (1.1 ml, 13.6 mmol) was added and the mixture was allowed to warm to room temperature. The resulting mixture was added over 5 minutes to a stirred mixture of phenol (1.25 g, 13.3 mmol) and triethylamine (7.0 ml, 50.6 mmol) in acetonitrile (30 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and dilute sodium bicarbonate solution. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title product (D7). MS (ES+) m/e 314/316 [M+H]+.

Provenance & Evidence