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

HRID 1599962Notes

Reaction equation

HRID 1599962 reaction equation
Cl[C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][S-:18].[Na+]>CN(C=O)C>[CH3:17][S:18][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 11780008HCID 11780008, compound

Product 1

HCID 11010829Ethyl 2-(methylthio)-4-(trifluoromethyl)benzoateYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Example 3 is repeated except that 2.53 g (10 mmol) of ethyl 2-chloro-4-(trifluoromethyl)benzoate are reacted with 0.77 g (11 mmol) of sodium thiomethoxide in 15 ml of DMF. 2.5 g of ethyl 2-methylmercapto-4-(trifluoromethyl)benzoate of high purity are obtained. It is therefore not necessary to purify by distillation.

Sources & evidence

ORD record
ord-d2e0628730b241a68f33f91d08c5431b
Source dataset
uspto-grants-1998_04
Patent number
US05744021

Reaction notes

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