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Fluorinated Building Blocks

No.138(August 2009)
F0665
Fluoroacetonitrile (1)
 Fluoroacetonitrile (1) is known as a versatile fluorinated building block in organic synthesis. For example, reaction of 1 with Grignard reagent 2, followed by treatment with NaCN and NH4Cl affords 3, which can subsequently be converted into fluorinated ornithine decarboxylase inhibitor 4.1) Alternatively, 1 can be converted into α-fluoroacrylonitrile derivative 6 by Horner-Emmons reaction using diphenylphosphonic chloride (5)2) and also affords α-fluoroaldehyde derivative 9 by reaction with 2-methyl-1,3-pentanediol (7)3).
 In addition, fluoroacrylate cation equivalent 10 is useful as a synthetic material for the preparation of 2-fluoroalkenecarboxylic acid 11,4) allylic amines containing fluoromethyl group, α,β-unsaturated ketones,5) and fluorine-containing cytosine derivatives6) which are useful for the development of oncology drugs.

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