Acetic Anhydride → Ethyl 2-(2-bromo-4,5-difluorobenzoyl)-3-ethoxyacrylate

HRID 1788659Notes

Reaction equation

HRID 1788659 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:18]([O-])([O-])[O:19][CH2:20][CH3:21].C(OC(=O)C)(=O)C>>[Br:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:3]=1[C:4]([C:6](=[CH:18][O:19][CH2:20][CH3:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 13912599Ethyl (2-bromo-4,5-difluorobenzoyl)acetateHCID 53630039Ethylorthoformate

Product 1

HCID 54231265Ethyl 2-(2-bromo-4,5-difluorobenzoyl)-3-ethoxyacrylateYield 79.7%

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl (2-bromo-4,5-difluorobenzoyl)acetate (52.0 g), ethyl orthoformate (36.6 g) and acetic anhydride (41.6 g) is heated at 150° C. for 2 hours. After the reaction, the reaction mixture is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:n-hexane=2:1) to give ethyl 2-(2-bromo-4,5-difluorobenzoyl)-3-ethoxyacrylate (49 g).

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:n-hexane=2:1)

Sources & evidence

ORD record
ord-7af6035e622f47afb28a3eccd209e00d
Source dataset
uspto-grants-1987_08
Patent number
US04684648

Reaction notes

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