Process for converting an alcohol to the corresponding fluoride

C - Chemistry – Metallurgy – 07 – B

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C07B 39/00 (2006.01) C07C 17/16 (2006.01) C07C 41/22 (2006.01) C07D 239/26 (2006.01)

Patent

CA 2349325

A process for preparing a fluoride from its corresponding alcohol comprises the steps of (a) forming a mixture comprising (i) at least one fluorinated, saturated aliphatic or alicyclic sulfonyl fluoride (for example, perfluorobutanesulfonyl fluoride) and (ii) at least one primary or secondary alcohol; and (b) adding a molar excess of at least one strong, aprotic, non-nucleophilic, hindered, double bond-containing, organic base (for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) to the mixture. The process is cost effective and provides excellent yields under variable reaction conditions.

Procédé de préparation d'un fluorure à partir de son alcool correspondant, qui consiste (a) à former un mélange comprenant (i) au moins un fluorure de sulfonyle aliphatique ou alicyclique fluoré, saturé ( par exemple du fluorure de perfluorobutanesulfonyle) et (ii) au moins un alcool primaire ou secondaire, et (b) à ajouter un surplus molaire d'au moins une base organique forte, aprotique, non nucléophile, empêchée, à double liaison (par exemple du 1,8-diazabicyclo[5.4.0]undéc-7-ène (DBU)) à ce mélange. Ledit procédé est peu onéreux et fournit d'excellents rendements dans des conditions de réaction variables.

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