Thionyl Chloride → 4-Acetoxy-3-fluorobenzoyl chloride

HRID 1589726Notes

Reaction equation

HRID 1589726 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[F:18])(=[O:7])[CH3:6]>CN(C)C=O.C1C=CC=CC=1>[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:3])=[O:14])=[CH:11][C:10]=1[F:18])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 193653054-Acetoxy-3-fluorobenzoic acid

Product 1

HCID 212027174-Acetoxy-3-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

2.90 ml of thionyl chloride was added to 2.50 g (12.6 mM) of 4-acetoxy-3-fluorobenzoic acid. Under stirring at room temperature, two drops of N,N-dimethylformamide (DMF) was added thereto, followed by refluxing for 40 minutes. After the reaction, dry benzene was added to the reaction mixture, followed by two times of distilling-off of excessive thionyl chloride under reduced pressure to obtain 4-acetoxy-3-fluorobenzoyl chloride.

Workup

  1. temperatureby refluxing for 40 minutes
  2. additionwas added to the reaction mixture

Sources & evidence

ORD record
ord-f410abdb5667411cb3a3f5b69161a42d
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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