Cyanuric chloride → HCID 49758603, compound

Participants

Reaction Steps

A solution of 1-iodo-2-fluorobenzene (2.22 g, 10 mmol) in THF (15 mL) was cooled in a dry-ice/acetone bath and then treated dropwise with a solution of nBuLi in cyclohexane (5 mL, 2M, 10 mmol) under nitrogen. The mixture was stirred cold for 30 minutes and then transferred by cannula into a solution of cyanuric chloride (1.84 g, 10 mmol) in THF (20 mL) along with a rinse with THF (5 mL). The mixture was stirred cold for 10 minutes and then allowed to warm to room temperature for 2 hours. The reaction was poured into a mixture of saturated sodium bicarbonate (25 mL) and water (25 mL) and stirred for 15 minutes. Treated with hexanes (50 mL), shaken in a separatory funnel and separated layers. The organic layer was dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to yield yellow oil. The oil was diluted with a small amount of dichloromethane and loaded onto 100 g of silica gel. The silica gel was eluted with 10% ethyl acetate/hexanes. The appropriate fractions were concentrated on a rotary evaporator to yield slightly yellow oil. The oil was diluted with chloroform and loaded onto 100 g of silica gel. The silica gel was eluted with ethyl acetate/hexanes (2.5%, 5%, 7.5%). The appropriate fractions were concentrated on a rotary evaporator to yield 2,4-dichloro-6-(2-fluorophenyl)-1,3,5-triazine (VIII) as a white solid (0.842 g). ESI/MS 244.0, 246.0, 248.0 (M+H).

Provenance & Evidence