4-Fluorobenzoic Acid → 4-Fluorobenzoyl chloride

HRID 888706Notes

Reaction equation

HRID 888706 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1>CN(C)C=O.ClC1C=CC=CC=1>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:3])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 678794-Fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (3.8 g, 32.1 mmol) was slowly added to a solution of 4-fluorobenzoic acid 1a (3.0 g, 21.4 mmol) and N,N-dimethylformamide (5 drops) in 15 mL of chlorobenzene under a stream of nitrogen gas. The mixture was stirred at 60° C. for 2 hr. The solvent was removed under reduced pressure to afford 4-fluorobenzoyl chloride 1b. Yield: 3.0 g (88%).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c85ae0635fdb4813a888479aefb4db9b
Source dataset
uspto-grants-2012_08
Patent number
US08252507B2

Reaction notes

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