Thionyl Chloride → 2,3-Difluorobenzoyl chloride

HRID 2386200Notes

Reaction equation

HRID 2386200 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 5195492,3-Difluorobenzoyl chlorideYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Difluorobenzoic acid (11.6 g, 0.07 mol), thionyl chloride (37.5 ml, 61.1 g, 0.5 mol) and toluene (80 ml) were heated at reflux for 3 h. The solution was cooled and the volatiles were removed in vacuo. The residue was azeotroped with toluene (2×30 ml) to give the product (10.8 g) as a clear yellow oil.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe solution was cooled
  3. customthe volatiles were removed in vacuo
  4. customThe residue was azeotroped with toluene (2×30 ml)

Sources & evidence

ORD record
ord-5147e5767bbb45c8b5eb51b073318dd3
Source dataset
uspto-grants-2012_09
Patent number
US08268823B2

Reaction notes

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