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

Participants

Reaction Conditions

Reaction Steps

To a 5-L reactor was added 2,4,6-trichloro-1,3,5-triazine (180 g, 976 mmol) and DCM (180 mL). To the solution cooled at 0° C. in a dry ice bath was added methylmagnesium bromide (390 mL, 1171 mmol) over 30 min while the reaction temperature was kept below rt. After the addition, the reaction mixture was placed in an ice-water bath to keep the internal temperature stable at 20° C. After the mixture was stirred overnight at rt, it was cooled to −20° C. and was slowly quenched with ice water (500 mL) (internal temperature was controlled below 0° C.). The mixture was allowed to warm to rt and was transferred to a separation funnel. The organic layer was washed with water (500 mL), and concentrated to afford 2,4-dichloro-6-methyl-1,3,5-triazine (127 g, 774 mmol, 79% yield) as a solid that was carried to the next step.

Provenance & Evidence