Thionyl Chloride → 3,4-Difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl ester

HRID 1991917Notes

Reaction equation

HRID 1991917 reaction equation
[C:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)=[CH:8][CH:7]=1)(O)=[O:2].S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][C:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)=[CH:8][CH:7]=1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 685379543,4-Difluoro-benzoic acid 4-(2-carboxy-vinyl)-phenyl ester

Product 1

HCID 723620523,4-Difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

About 10 g (about 21.68 mmol) of 3,4-difluoro-benzoic acid 4-(2-carboxy-vinyl)-phenyl ester was dissolved in about 200 ml of methylene chloride, and about 2.84 g (23.848 mmol) of thionyl chloride (SOCl2) was added thereto. Thereafter, the reaction mixture was stirred at about 35° C. for about 6 hours, followed by removing the solvent. Subsequently, a vacuum drying process was conducted, thus obtaining the desired compound (Yield about 90%).

Workup

  1. customby removing the solvent
  2. customSubsequently, a vacuum drying process

Sources & evidence

ORD record
ord-72af5323641546aea381b79ab4b5cbc8
Source dataset
uspto-grants-2010_01
Patent number
US07646014B2

Reaction notes

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