Thionyl Chloride → Methyl 2,4-Difluorobenzoate

HRID 636748Notes

Reaction equation

HRID 636748 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[C:16]([O-])(O)=O.[Na+]>CO>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 741022,4-Difluorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2782897Methyl 2,4-DifluorobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) in methanol (15 ml) was cooled to 0° C. in ice-water bath. To the mixture was added dropwise a solution of thionyl chloride (1.46 ml, 20.02 mmol) in methanol (10 ml). The mixture was gradually warmed to room temperature and stirred for 24 hours. The mixture was added to sat. NaHCO3 aqueous solution, extracted three times with ether and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (1.6743 g; 97%).

Workup

  1. extractionextracted three times with ether
  2. dry with materialdried over MgSO4
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography (hexane/ether=5/1)

Sources & evidence

ORD record
ord-abb0af6022ff40ec94972f5d9cace742
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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