Fries rearrangement: scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1, 2-diethoxy-3-fluorobenzene
…, MY Bhoite, AK Gangopadhyay, K Nagarajan…
Index: Yerande, Swapnil G.; Shendage, Deepak M.; Wakchaure, Prasad B.; Phadtare, Ganesh R.; Bhoite, Madhavrao Y.; Gangopadhyay, Ashok Kumar; Nagarajan, Kuppuswamy; Rupp, Richard Helmut Tetrahedron Letters, 2014 , vol. 55, # 15 p. 2426 - 2429
Full Text: HTML
Citation Number: 0
Abstract
Abstract Lewis acid catalyzed Fries rearrangement of 2-fluorophenyl acetate (3) was performed on kg scale. The ortho5 and para4 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.
Related Articles:
[Stefanidis, Dimitrios; Cho, Sayeon; Dhe-Paganon, Sirano; Jencks, William P. Journal of the American Chemical Society, 1993 , vol. 115, # 5 p. 1650 - 1656]
[Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew Journal of the American Chemical Society, 1989 , vol. 111, # 7 p. 2647 - 2652]
[Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew Journal of the American Chemical Society, 1989 , vol. 111, # 7 p. 2647 - 2652]