Halogenation of trifluoromethoxy and bis(trifluoromethoxy)benzene

Add time:08/02/2019    Source:sciencedirect.com

Controlled chlorination of trifluoromethoxybenzene produced the mono-, di-, tri-, and tetrachloro derivatives. Two isomers were detected at each level of substitution. Exhaustive chlorination and bromination of 1,3- and 1,4-bis(trifluoromethoxy)-benzene yielded isomeric mixtures of only the disubstituted bis(trifluoromethoxy)benzenes. No hydrolysis of the -OCF3 group was detected in any halogenations. The configuration of all the products was determined by 1H and 19F nmr. A through-space hydrogen-fluorine coupling of 0.7 – 1.3Hz between the -OCF3 substituent and the ortho proton was observed in all the halogenated products. The polychlorinated derivatives all exhibited good thermal stability at 200°–250°.

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