2-Fluorobenzoic acid → 2-Fluorobenzoyl chloride

HRID 1049062Notes

Reaction equation

HRID 1049062 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].O=S(Cl)[Cl:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 99352-Fluorobenzoic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 98082-Fluorobenzoyl chlorideYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To 100 mL of toluene were added 0.714 mol of 2-fluorobenzoic acid (100 g) then the mixture was heated to 50° C. and added 5.7 mol (414 mL) sulfoxide chloride. The reaction mixture was refluxed for 7 h. After completion of the reaction, sulfoxide chloride was evaporated to give 2-fluorobenzoyl chloride 79 g. Yield: 70%.

Workup

  1. temperatureThe reaction mixture was refluxed for 7 h
  2. customwas evaporated

Sources & evidence

ORD record
ord-f55ff409464b48198429f116c52c46cf
Source dataset
uspto-grants-2016_07
Patent number
US09382232B2

Reaction notes

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