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

HRID 1019348Notes

Reaction equation

HRID 1019348 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 solution of methyl 2-chloro-4-trifluoromethylbenzoate (1.19 g, 0.005M) in anhydrous N-methylpyrrolidinone (10 ml) at 5° C. After 3 hours the mixture was acidified, extracted (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 (ether)
  2. washwashed (water)
  3. customevaporated

Sources & evidence

ORD record
ord-9db295afc527454e99be3521ae7989a5
Source dataset
uspto-grants-2002_11
Patent number
US06486356B2

Reaction notes

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