Acetic Anhydride → Ethyl 2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate

HRID 2226491Notes

Reaction equation

HRID 2226491 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([O-:13])([O-])[O:9][CH2:10][CH3:11].[F:14][CH:15]([F:37])[O:16][C:17]1[C:18]([F:36])=[C:19]([C:28]([N+:33]([O-:35])=[O:34])=[C:29]([F:32])[C:30]=1[F:31])[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=O)=[O:21]>>[F:37][CH:15]([F:14])[O:16][C:17]1[C:18]([F:36])=[C:19]([C:28]([N+:33]([O-:35])=[O:34])=[C:29]([F:32])[C:30]=1[F:31])[C:20]([C:22](=[CH:23][O:25][CH2:26][CH3:27])[C:8]([O:9][CH2:10][CH3:11])=[O:13])=[O:21]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 15282968Ethyl 3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoylacetateHCID 53630039Ethylorthoformate

Product 1

HCID 54209226Ethyl 2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate

Procedure

38 ml of acetic anhydride and 11 ml of ethyl orthoformate were added to the whole of the ethyl 3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoylacetate [(XV), R1 =--OCHF2, R3' =NO2, R17 =C2H5, X=X'=F] prepared as described in step (b) above, and then the mixture was heated under reflux for 3 hours; the excess acetic anhydride and ethyl orthoformate were then removed by evaporation under reduced pressure, to give 20.6 g of ethyl 2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate as a red liquid.

Workup

  1. custom' =NO2, R17 =C2H5, X=X'=F] prepared
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. customthe excess acetic anhydride and ethyl orthoformate were then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2ea12081de304709af2e3fcac879be00
Source dataset
uspto-grants-1994_09
Patent number
US05348961

Reaction notes

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