3,4-Difluorobenzoic acid → 1-(3,4-Difluorophenyl)ethan-1-one
Reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([N+]([O-])=O)[CH:3]=1.F[C:16]1C=C(C=CC=1F)C(O)=O>>[CH3:16][C:6]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=1)=[O:8]Participants
3
Procedure
Briefly, the benzoyl ester derivatives of formula II are prepared by reacting 5-fluoro-4-halo-2-nitrobenzoic acid with a chlorinating agent, such as thionyl chloride or trichlorophosphorous, followed by reacting the acid chloride so formed with a dialkylmalonate. The 4,5-difluoro-2-nitrobenzoic acid starting material can be prepared by nitration in mixed acid of 3,4-difluorobenzoic acid, which is obtained by oxidation 3,4-difluoroacetophenone. The 4- chloro-5-fluoro-2-nitrobenzoic acid starting material can be obtained by the following process:
Sources & evidence
- ORD record
- ord-e410c75b2d4843988731bcdd374b5e1d
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05138088
Reaction notes
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