Reaction #4361

ord-cc19d9ec45394266839c589e505a7929

Reaction equation

CCOC(=O)CC(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl
ethyl (2,4-dichloro-5-fluoro-3-nitrobenzoyl)-acetate
CCOC(OCC)OCC
triethyl orthoformate
CC(=O)OC(C)=O
acetic anhydride
→
CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl
Ethyl 2-(2,4-dichloro-5-fluoro-3-nitro-benzoyl)-3-ethoxyacrylate

Reactants

CCOC(=O)CC(=O)c1cc(F)c(Cl)c([N+](=O)[O-])c1Cl
ethyl (2,4-dichloro-5-fluoro-3-nitrobenzoyl)-acetate
CCOC(OCC)OCC
triethyl orthoformate
CC(=O)OC(C)=O
acetic anhydride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe mixture is then concentrated in vacuo and 270 g of ethyl benzoyl-ethoxy-acrylate
  2. 2
    Otherare obtained as an oily residue

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 benzoyl-ethoxy-acrylate are obtained as an oily residue.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725595uspto-grants-1988_02