4-Fluorobenzoic Acid → 4-Fluorobenzoyl chloride

HRID 1381109Notes

Reaction equation

HRID 1381109 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>CN(C)C=O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 678794-Fluorobenzoyl chlorideYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 4-fluorobenzoic acid (0.15 mol), thionyl chloride (0.45 mol) and dimethylformamide (5 drops) in chloroform (200 ml) was heated at reflux for 16 hours. Volatiles were removed from the cooled solution in vacuo. The residue was diluted with carbon tetrachloride (100 ml) and the mixture evaporated in vacuo to remove residual thionyl chloride. The residue was distilled affording 19.7 g of a clear oil (83% yield); bp 110°-112° C. at 40 mm of Hg. Spectral data are consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customVolatiles were removed from the cooled solution in vacuo
  4. additionThe residue was diluted with carbon tetrachloride (100 ml)
  5. customthe mixture evaporated in vacuo
  6. customto remove residual thionyl chloride
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-9a9d832692334d21b740336356c5e2e3
Source dataset
uspto-grants-1986_04
Patent number
US04585773

Reaction notes

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