4-Fluorobenzoic Acid → 4-Fluorobenzoyl chloride

HRID 2286481Notes

Reaction equation

HRID 2286481 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>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 678794-Fluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

4-Fluorobenzoic acid, 14.0 g (0.1 mole) is refluxed for 30 minutes in 50 ml of thionyl chloride (SOCl2) and 1 drop of dimethylformamide (DMF). The thionyl chloride is removed under vacuum and azeotroped with 50 ml of benzene to give 4-fluorobenzoyl chloride as an oil.

Workup

  1. customThe thionyl chloride is removed under vacuum
  2. customazeotroped with 50 ml of benzene

Sources & evidence

ORD record
ord-2f64ca0b11d14909bc34351442f6a4fd
Source dataset
uspto-grants-1981_05
Patent number
US04265905

Reaction notes

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