Hydrochloric Acid → Methyl 2-chloro-4-(methylthio)benzoate

HRID 1828799Notes

Reaction equation

HRID 1828799 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.[CH3:13][S-:14].[Na+].Cl>CN(C)C=O>[Cl:12][C:4]1[CH:3]=[C:2]([S:14][CH3:13])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Product 1

HCID 13961932Methyl 2-chloro-4-(methylthio)benzoateYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) was added sodium thiomethoxide (459 mg) under ice-cooling and the mixture was stirred for 2 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined, washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=10/1) to give methyl 2-chloro-4-(methylthio)benzoate (835 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe resulting product was extracted 3 times with diethyl ether
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-07ed599f3bff4baf9d760a2c15916697
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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