4-Cyanobenzoic acid → 4-Cyanobenzoyl chloride

HRID 2202090Notes

Reaction equation

HRID 2202090 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)#[N:2].S(Cl)([Cl:14])=O>ClCCl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 120874-Cyanobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 801724-Cyanobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyanobenzoic acid (5 g, 33.98 mmol, 1.00 equiv) in dichloromethane (50 mL) was added thionyl chloride (25 mL) dropwise with stirring. The resulting solution was refluxed for 4 h. The reaction mixture was cooled to room temperature and concentrated under vacuum to give 3 g of crude 4-cyanobenzoyl chloride as a brown solid. The crude was used in the next step without further purification.

Workup

  1. temperatureThe resulting solution was refluxed for 4 h
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-04ed0d00b60e48399511d5a4cdddb767
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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