Cyanuric chloride → 2,4-Dichloro-6-methyl-1,3,5-triazine

Participants

Reaction Steps

Methyl magnesium bromide (3M in ethyl ether, 9 ml, 27 mmol) was added dropwise over 10 min to a cooled (0° C.) solution of 2,4,6-trichloro-1,3,5-triazine (5 g, 27 mmol) in tetrahydrofuran (270 ml). The reaction mixture was stirred at ambient temperature for 20 hours and was then quenched with saturated NH4Cl (aq) (100 mL). The aqueous layer was extracted using dichloromethane (3×50 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated to remove the most of solvent. Celite was then added to the solution and the resulting suspension was concentrated to dryness under vacuum and purified using silica gel chromatography (120 g SiO2 gel column; solvent dichloromethane/hexane from 0 to 30%) to give 2,4-dichloro-6-methyl-1,3,5-triazine (1.38 g of 90% purity, 7.57 mmol, 28%). MS (ES) m/e 164 [M+H]+.

Provenance & Evidence