Process for selectively ortho-fluorinating substituted...

C - Chemistry – Metallurgy – 07 – C

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C07C 43/225 (2006.01) C07B 39/00 (2006.01) C07C 41/22 (2006.01) C07C 45/63 (2006.01) C07C 49/807 (2006.01) C07C 231/12 (2006.01) C07C 233/65 (2006.01) C07C 269/06 (2006.01) C07C 271/06 (2006.01) C07C 303/40 (2006.01) C07C 311/16 (2006.01) C07C 315/04 (2006.01) C07C 317/32 (2006.01) C07C 311/21 (2006.01)

Patent

CA 2096928

The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromaticcompound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.

L'invention décrit une méthode pour préparer sélectivement des dérivés de substitution ortho-fluorés de composés aromatiques, dans laquelle on met en contact un aromatique renfermant un substituant apte à induire une métallation en ortho avec un réactif de métallation dans des conditions de réaction permettant d'obtenir un aromatique métallisé en ortho. On fait réagir ce dernier composé avec un réactif de fluoration électrophile dans des conditions permettant d'obtenir l'aromatique fluoré en ortho, lequel est ensuite récupéré à partir du mélange réactionnel. La méthode, qui utilise un intermédiaire de métallation avant l'étape de fluoration électrophile, évite les problèmes liés aux procédés classiques de ce type de fluoration, où on ne fait pas appel à un intermédiaire permettant d'exercer un contrôle stéréospécifique sur le processus.

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