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Acetic Anhydride → Ethyl 2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl)-3-ethoxyacrylate

HRID 1608348
Notes
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Reaction equation

HRID 1608348 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6](=[O:19])[C:7]1[CH:12]=[C:11]([F:13])[C:10]([Cl:14])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]=1[Cl:18])[CH3:2].[CH:21](OCC)(OCC)[O:22][CH2:23][CH3:24].C(OC(=O)C)(=O)C>>[Cl:18][C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[C:10]([Cl:14])[C:11]([F:13])=[CH:12][C:7]=1[C:6]([C:5](=[CH:21][O:22][CH2:23][CH3:24])[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 13733140Ethyl 2,4-dichloro-5-fluoro-3-nitro-beta-oxobenzenepropanoate

Product 1

HCID 53944414Ethyl 2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl)-3-ethoxyacrylate

Procedure

244.8 g of ethyl(2,4-dichloro-5-fluoro-3-nitrobenzoyl)-acetate are heated at 150°-160° C. with 166 g of triethyl orthoformate and 185 g of acetic anhydride for 3 hours. The mixture is then concentrated in vacuo and 270 g of ethyl 2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl)-3-ethoxy-acrylate are obtained as an oily residue.

Workup

  1. concentrationThe mixture is then concentrated in vacuo and 270 g of ethyl 2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl)-3-ethoxy-acrylate
  2. customare obtained as an oily residue

Sources & evidence

ORD record
ord-94c028a0cb1f47c3825cef3e8b57aded
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04870182

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes