Hydrochloric Acid → 2,4-Dichloro-6-(2,4-dimethylphenyl)-1,3,5-triazine

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Reaction Steps

17.0 g (0.70 mol) of iodine-activated magnesium turnings in 25 ml of anhydrous THF are heated briefly to 60° C. Then 154.9 g (0.70 mol) of 4-bromo-m-xylene (in c. 90% purity) and 155 ml of THF are added dropwise over 30 min and the mixture is heated for 2 hours to reflux. After cooling, the Grignard solution is added over 1.5 hours to a mixture of 43.0 g (0.233 mol) of cyanuric chloride and 150 ml of THF, while keeping the temperature of the mixture in the range from 0° to 10° C. The mixture is then diluted with 210 ml of toluene, the resultant suspension is poured into 220 g of 12% aqueous HCl, the organic phase is separated, washed with a total amount of 280 g of water and concentrated. The resultant material is recrystallised from 2-butanol, giving the title compound with a melting point of 135.5°-137° C. in a yield of 79.8%.

Provenance & Evidence