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Fries rearrangement: scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1,2-diethoxy-3-fluorobenzene |
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| Authors: | Swapnil G Yerande Deepak M Shendage Prasad B Wakchaure Ganesh R Phadtare Madhavrao Y Bhoite Ashok Kumar Gangopadhyay Kuppuswamy Nagarajan Richard Helmut Rupp |
| Institution: | 1. Acoris Research (A Division of Hikal Ltd), 3A, International Biotech Park, Hinjewadi, Pune 411 057, Maharashtra, India;2. Hikal R&D Centre, No. 32/1, Kalena Agrahara, Bannerghatta Road, Bangalore 560 076, Karnataka, India |
| 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. |
| Keywords: | Acylation Lewis acid Fries rearrangement Dakin oxidation Process development |
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