Thionyl Chloride → 3-Chloro-2-fluorobenzoyl chloride

HRID 2386203Notes

Reaction equation

HRID 2386203 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:14])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3029313-Chloro-2-fluorobenzoic acid

Product 1

HCID 27735983-Chloro-2-fluorobenzoyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloro-2-fluorobenzoic acid (10.0 g, 0.06 mol), thionyl chloride (31 ml, 50 g, 0.4 mol) and dry toluene (40 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 (11.5 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-318696b60fb4499ba490284f112a021f
Source dataset
uspto-grants-2012_09
Patent number
US08268823B2

Reaction notes

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