Sodium methanethiolate → Methyl 2-(methylthio)-4-(trifluoromethyl)benzoate

HRID 1836754Notes

Reaction equation

HRID 1836754 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]>CN1CCCC1=O>[CH3:1][S:2][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 23499962Methyl 2-chloro-4-(trifluoromethyl)benzoate

Product 1

HCID 10944828Methyl 2-(methylthio)-4-(trifluoromethyl)benzoateYield 94.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Dry sodium thiomethoxide (0.385 g. 0.0055M) was added to a stirred solution of methyl 2-chloro-4-trifluoromethylbenzoate (1.19 g, 0.005M) in anhydrous N-methylpyrrolidinone (10 ml) at 5° C. The mixture was acidified and extracted (t-butyl methyl ether), washed (water) and evaporated to give methyl 2-methylthio-4-trifluoromethylbenzoate (1.18 g, 94% yield). 1H-nmr 2.44(s,3H). 3.89(s,3H). 7.33(1H), 7.41(1H), 8.02(1H).

Workup

  1. extractionextracted (t-butyl methyl ether)
  2. washwashed (water)
  3. customevaporated

Sources & evidence

ORD record
ord-46dd300db15545fd944defaabf9c44cf
Source dataset
uspto-grants-2004_08
Patent number
US06777575B2

Reaction notes

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