Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 18356786, compound

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Reaction Conditions

Reaction Steps

31.3 ml 1.6M n-butyllithium in hexane are added at −70° C. to a solution of 11.25 g 4-bromo-benzotrifluorid in 50 ml diethylether. After stirring for 15 min. the solution is warmed to −30° C. and added to a −30° C. cold solution of 8.0 g 4-chloro-2-methylthio-pyrimidine in 50 ml ether. The mixture is stirred for 30 min. at −30° C. and another 30 min. at 0° C., then quenched with a mixture of 3.2 ml acetic acid, 0.5 ml water and 10 ml tetrahydrofuran (THF). Immediately after quenching, a solution of 11.8 g dichlorodicyanobenzoquinone (DDQ) in 50 ml THF is added and stirring is continued for 5 min. at room temperature. It is again cooled to 0° C. and 20 ml 10% aqueous sodium hydroxide are added. After stirring for 5 min. at 0° C. the organic layer is separated, dried and chromatographed to yield 10.3 g of the title compound (m.p. 93-96° C.).

Provenance & Evidence