Toluene → 3,5-Difluoro-4-methoxybenzoyl chloride

HRID 385085Notes

Reaction equation

HRID 385085 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:13])[C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].C1(C)C=CC=CC=1.S(Cl)([Cl:23])=O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:13])[C:10]=1[O:11][CH3:12])[C:5]([Cl:23])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 27369873,5-Difluoro-4-methoxybenzoic acid

Product 1

HCID 177506623,5-Difluoro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3,5-difluoro-4-methoxybenzoic acid (310 mg), toluene (3 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.14 mL) were added to the solution, and then the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (347 mg) as a brown oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-26ab506ce336413da84f7b6eecec6571
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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