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

Participants

Reaction Steps

Methylmagnesium bromide (9.00 mL of a 3.0 M solution in Et2O, 27.1 mmol, 1.00 equiv) was added dropwise over 1 h to a cooled (0° C.) solution of cyanuric chloride (5.00 g, 27.1 mmol, 1.00 equiv) in THF (270 mL). The reaction mixture was stirred at room temperature overnight and was then quenched with sat NH4Cl (aq). The aqueous layer was extracted 3 times using ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified using silica gel chromatography (0-40% CH2Cl2/hexanes) to afford 1.5 g (34%) of the title compound. MS (ES+): m/e 164.0 [M+H]+.

Provenance & Evidence