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

HRID 249293Notes

Reaction equation

HRID 249293 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=O)[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[Cl:15])[CH3:2].[CH2:18]([O:20][CH:21](OCC)OCC)[CH3:19].C(OC(=O)C)(=[O:30])C>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:6](=[O:30])[C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[Cl:15])=[CH:21][O:20][CH2:18][CH3:19])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 536624732-Chloro-4,5-difluoro-alpha-oxobenzenepropanoic acid ethyl ester

Product 1

HCID 54163438Ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-ethoxyacrylate

Procedure

2-Chloro-4,5-difluoro-α-oxo-benzenepropanoic acid ethyl ester (20 g, 76 mmol), triethylorthoformate (17.0 g, 115 mmol) and acetic anhydride (19.5 g, 191 mmol) were combined and heated to reflux for 3 hours. Excess solvent was removed in vacuo to provide the crude title product, which was used without purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customExcess solvent was removed in vacuo

Sources & evidence

ORD record
ord-6a1227d77b4c4ea1b9035e0775679ef6
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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