Fries rearrangement: scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1,2-diethoxy-3-fluorobenzene

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• 作者：Swapnil G. Yerande^a ; ^{swapnil_yerande@acorisresearch.com" class="auth_mail} ; Deepak M. Shendage^a ; Prasad B. Wakchaure^a ; Ganesh R. Phadtare^a ; Madhavrao Y. Bhoite^a ; Ashok Kumar Gangopadhyay^a ; Kuppuswamy Nagarajan^b ; Richard Helmut Rupp^a
• 关键词：Acylation ; Lewis acid ; Fries rearrangement ; Dakin oxidation ; Process development
• 刊名：Tetrahedron Letters
• 出版年：9 April, 2014
• 年：2014
• 卷：55
• 期：15
• 页码：2426-2429
• 全文大小：584 K

文摘

Lewis acid catalyzed Fries rearrangement of 2-fluorophenyl acetate (3) was performed on kg scale. The ortho 5 and para 4 isomers obtained were separated in an industrially feasible way. Compound 4 was then converted into fluorinated building block 3-fluoro-4-methoxybenzoyl chloride (1) while compound 5 was converted into 1,2-diethoxy-3-fluorobenzene (2) in high yields.