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

HRID 1699919Notes

Reaction equation

HRID 1699919 reaction equation
[CH3:1][S-:2].[Na+].Br[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([Cl:15])[CH:6]=1.Cl>CN(C)C=O>[Cl:15][C:7]1[CH:6]=[C:5]([S:2][CH3:1])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

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

Sodium thiomethoxide (459 mg) was added to a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) under ice-cooling, and the mixture was stirred for 2 hr. 1N Hydrochloric acid was added to the reaction mixture and the resulting product was extracted three times with 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 subjected to silica gel column chromatography (hexane/ethyl acetate=10/1) to give the objective compound (835 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe resulting product was extracted three times with 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-8d81f1f76f5b48c5b4ce537a390dd5f9
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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