Thionyl Chloride → 4-Bromo-2,6-dichlorobenzoyl chloride

HRID 2201773Notes

Reaction equation

HRID 2201773 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6](O)=[O:7])=[C:4]([Cl:12])[CH:3]=1.S(Cl)([Cl:15])=O>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([Cl:15])=[O:7])=[C:4]([Cl:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 225718224-Bromo-2,6-dichlorobenzoic acid

Product 1

HCID 225717234-Bromo-2,6-dichlorobenzoyl chlorideYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2,6-dichlorobenzoic acid (2 g, 7.4 mmol), and thionyl chloride (5.5 mL, 74 mmol) in dichloromethane (30 mL) was heated under refluxed for 5 hours. The reaction mixture was cooled to room temperature and concentrated under vacuum. The resulting mass was taken up in dichloromethane (20 mL) and concentrated under vacuum. The process was repeated 2-3 times to remove excess thionyl chloride. 4-Bromo-2,6-dichlorobenzoyl chloride (2.2 g, 100%) thus formed was used as such for the next step.

Workup

  1. temperatureunder refluxed for 5 hours
  2. concentrationconcentrated under vacuum
  3. concentrationconcentrated under vacuum
  4. customto remove excess thionyl chloride

Sources & evidence

ORD record
ord-017211d0c57640b8aa43fdaa657cade5
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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