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

HRID 1762741Notes

Reaction equation

HRID 1762741 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH:18](OCC)(OCC)[O:19][CH2:20][CH3:21]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10](=[O:17])[C:11](=[CH:18][O:19][CH2:20][CH3:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 14423850Ethyl 3-(2-chloro-4,5-difluorophenyl)-3-oxopropanoate

Product 1

HCID 54163438Ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-ethoxyacrylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 14.5 g of 2-chloro-4,5-difluoro-β-oxobenzenepropanoic acid, ethyl ester and 12.27 g of triethyl orthoformate in 13 ml of acetic anhydride was heated at 150° C. for 2 hours and then evaporated to dryness, giving 16.59 g of the desired product as an oil.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-41ed53989b1949c6b0e5fad7bdbe41cf
Source dataset
uspto-grants-1989_05
Patent number
US04833270

Reaction notes

Loading…