Sodium methanethiolate → Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

HRID 1836753Notes

Reaction equation

HRID 1836753 reaction equation
[CH3:1][S-:2].[Na+].[Na+].Cl[C:6]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8]([O-:10])=[O:9]>CN1CCCC1=O>[CH3:1][S:2][C:6]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 23679785HCID 23679785, compound

Product 1

HCID 11085762Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-Yield 100.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of anhydrous sodium thiomethoxide (0.39 g, 0.00525M), 2-chloro-4-trifluoromethylbenzoic acid sodium salt (1.23 g, 0.005M) and anhydrous N-methylpyrrolidinone (10 ml, containing less than 0.01% of water) was heated at 90° C. for 2 hours. The mixture was cooled to 20° C., acidified and extracted (t-butyl methyl ether). The extract was washed (water) and evaporated to give 2-methylthio-4-trifluoromethylbenzoic acid (1.18 g, 100% yield). 1H-nmr 2.40(s,3H). 7.30(1H), 7.38(1H), 8.07(1H). The purity of the product was greater than 95%.

Workup

  1. temperatureThe mixture was cooled to 20° C.
  2. extractionextracted (t-butyl methyl ether)
  3. washThe extract was washed (water)
  4. customevaporated

Sources & evidence

ORD record
ord-1f5f4f049f154d6aa17eaac0578354a1
Source dataset
uspto-grants-2004_08
Patent number
US06777575B2

Reaction notes

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