Synthesis and pharmacological properties of 1,2-bis(fluoromethoxy)1,1,3,3,3-pentafluoropropane

Fluoromethyl 2-methoxy-2,2-difluoro-1-(trifluoromethyl)-ethyl ether (compound B), a fluorinated diether derived from the anesthetic sevoflurane, was reacted with bromine trifluoride. With proper control of reaction temperature, a single product, 1,2-bis(fluoromethoxy)-1,1,3,3,3-pentafluoropropane (BFPP), was obtained in 58% yield. In the rat model, BFPP exhibited enhanced metabolic stability both in vivo and in liver microsomal preparations, evidenced by a reduction in fluoride release. Both compound B and BFPP were sedative/hypnotics in this animal, when administered intravenously. The sleep times of animals given BFPP were approximately six times longer than those of animals administered an equal dose of compound B.