Ammonia → Ethyl(4-amino-2,3,5,6-tetrafluorobenzoyl)acetate
Reaction equation
FC1C(F)=CC(F)=C(F)C=1CC(O)=O.[NH2:15]C1C(F)=C(F)C(CC(O)=O)=C(F)C=1F.N.[NH2-].[Na+].[F:33][C:34]1[C:47]([F:48])=[C:46](F)[C:45]([F:50])=[C:44]([F:51])[C:35]=1[C:36]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:37]>>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][C:36](=[O:37])[C:35]1[C:34]([F:33])=[C:47]([F:48])[C:46]([NH2:15])=[C:45]([F:50])[C:44]=1[F:51])[CH3:43]Participants
6
Procedure
The [4-amino(mono- or poly-fluoro)phenyl]alkanoic acids and esters required as intermediates are prepared by a sequence of reactions involving nitration of a suitable phenylalkanoic acid followed by reduction of the nitro group. For example, 2,3,5,6-tetrafluorophenylacetic acid is converted to 4-amino-2,3,5,6-tetrafluorophenylacetic acid by this method. The [4-amino-(mono- or poly-fluoro)benzoyl]alkanoic acids and esters are prepared by the reaction of ammonia or sodium amide with (4-halobenzoyl)alkanoic acids. For example, the reaction of sodium amide with ethyl 2,3,4,5,6-pentafluorobenzoylacetate yields ethyl(4-amino-2,3,5,6-tetrafluorobenzoyl)acetate.
Workup
- customare prepared by a sequence of reactions
Sources & evidence
- ORD record
- ord-44759f576f0e49e699f30aa3e91ca86e
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04333940
Reaction notes
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