Reduction of aromatic halogenides

C - Chemistry – Metallurgy – 07 – B

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C07B 31/00 (2006.01) C07C 1/26 (2006.01) C07D 223/00 (2006.01) C07D 307/00 (2006.01) C07D 333/10 (2006.01) C07D 491/10 (2006.01) C07D 491/20 (2006.01)

Patent

CA 2289992

The invention relates to the reduction of (hetero)aromatic halogenides of general formula (I) Ar-Xn to compounds of general formula (II) Ar-Hn. To achieve this, a reduction agent is used, in particular a hydride reactant such as lithium aluminium hydride (LiAlH4) in the presence of oxygen, in particular in the form of an oxygen-inert gas mixture. Reduction in the presence of oxygen gives a good yield in short reaction times, even when working on a semi- industrial or industrial basis. Reduction using LiAlH4 in the presence of oxygen can also be used to reduce complicated heteroaromatic halogenides, for instance for reducing bromonarwedine ketone acetal to narwedine ketone acetal on an industrial scale.

L'invention concerne la réduction d'halogénures (hétéro)aromatiques de la formule générale (I) Ar-X¿n? en composés de la formule générale (II) Ar-H¿n?, réduction dans laquelle on utilise un agent de réduction, en particulier un réactif hydrure comme l'hydrure d'aluminium et de lithium (LiAlH¿4?), en présence d'oxygène, en particulier sous forme d'un mélange d'oxygène et de gaz inerte. La réduction en présence d'oxygène donne de bons rendements pour des temps de réaction courts même dans des installations semi-industrielles ou industrielles. La réduction avec LiAlH¿4? en présence d'oxygène convient également à la réduction d'halogénures hétéroaromatiques complexes, par exemple à la réduction de cétal de bromonarwedine en cétal de narwedine à échelle industrielle.

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