Cyanuric chloride → 2,4-Dichloro-6-(2,5-dichlorophenyl)-1,3,5-triazine

Participants

Reaction Conditions

Reaction Steps

Alternatively, to a solution of 2,5-dichloro-iodobenzene (3.1 g, 11.4 mmol), hexamethylphosphoramide (6.6 ml) and tetrahydrofuran (20 ml), cooled to −78° C., was added a solution of tert-butyl lithium in pentane (1.7 M, 8.7 ml, 14.8 mmol) over 20 minutes. After stirring at −78° C. for 3 hours, a solution of cyanuric chloride (3.14 g, 17.1 mmol) in tetrahydrofuran (15 ml) was added over 15 minutes. After stirring at −78° C. for 1 hour, the mixture was warmed to −20° C. over 30 minutes. The reaction was quenched by slow addition of hydrochloric acid (1 M, 20 ml). The mixture was diluted with water (50 ml) and extracted with dichloromethane (3×40 ml). The combined extracts were washed with water (2×50 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (3:5) to provide 2,4-dichloro-6-(2,5-dichloro-phenyl)-[1,3,5]triazine (1.98 g, 59% yield).

Provenance & Evidence