Benzoic Acid → Benzoyl fluoride

HRID 1283934Notes

Reaction equation

HRID 1283934 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([OH:18])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[Na+]>C(Cl)Cl>[C:10]([F:7])(=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 5235Sodium FluorideHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 67999Benzoyl fluorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride, 2.5 ml (0.02 mole) was slowly added to a stirred solution of 2.44 g (0.02 mole) of benzoic acid in 20 ml methylene chloride cooled to 0°. Powdered sodium fluoride, 1 g, was added to remove the HF, and the reaction mixture was filtered. The filtrate was distilled to give 1.98 g (80%) of benzoyl fluoride as a colorless liquid, bp 50° (10 mm) (identified by its infrared spectrum).

Workup

  1. temperaturecooled to 0°
  2. customto remove the HF
  3. filtrationthe reaction mixture was filtered
  4. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-9ac1606dbfc34d0c95d26b0369b2b340
Source dataset
uspto-grants-1976_08
Patent number
US03976691

Reaction notes

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