1,2,3-Trifluoro-4-nitrobenzene → 3,4-Difluoro-2-(3,5-bis-tert-butylcarbamoyl-phenoxy)nitrobenzene
Reaction equation
[F:1][C:2]1[C:3](OC2C=C(C#N)C=C(C#N)C=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[C:23]([NH:27][C:28]([C:30]1[CH:31]=[C:32]([O-:43])[CH:33]=[C:34]([C:36](=[O:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[Na+].FC1C(F)=C(F)C=CC=1[N+]([O-])=O>>[F:1][C:2]1[C:3]([O:43][C:32]2[CH:31]=[C:30]([C:28](=[O:29])[NH:27][C:23]([CH3:26])([CH3:24])[CH3:25])[CH:35]=[C:34]([C:36](=[O:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:33]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]Participants
Procedure
In another embodiment of the present invention there is provided a process for the preparation of a compound according to formula III wherein R2 is 3,5-dicyano-phenyl which process further comprises (i) contacting sodium 3,5-bis-tert-butylcarbamoyl-phenolate with 2,3,4-trifluoronitrobenzene in an appropriate solvent at temperatures from about −30° C. up to about 40° C. to afford a 3,4-difluoro-2-(3,5-bis-tert-butylcarbamoyl-phenoxy)nitrobenzene; and (ii) contacting 3,4-difluoro-2-(3,5-bis-tert-butylcarbamoyl-phenoxy)nitrobezene with phosphorus oxychloride or a similar dehydrating agent to afford 3,4-difluoro-2-(3,5-dicyano-phenoxy)nitrobenzene III (R2=3,5-dicyanophenyl). The ether can be convert to IV (R2=3,5-dicyanophenyl) as described below.
Workup
- customIn another embodiment of the present invention there is provided a process
- customfor the preparation of a compound
- customfrom about −30° C. up to about 40° C.
Sources & evidence
- ORD record
- ord-8f2bc2d933b840c0b1c13e865d4cd40c
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291729B2
Reaction notes
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