Dimethylformamide → Methyl 2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoate

HRID 41857Notes

Reaction equation

HRID 41857 reaction equation
F[C:2]1[C:3]([CH3:19])=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[C:5]([O:7][CH3:8])=[O:6].CN(C)C=O.[CH3:25][S-:26].[Na+]>C(OCC)(=O)C>[CH3:19][C:3]1[C:2]([S:26][CH3:25])=[C:11]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 86661429HCID 86661429, compound

Product 1

HCID 86661431Methyl 2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoateYield 55.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.1 g (7.34 mmol) of methyl 3-fluoro-2-methyl-4-(pentafluoroethyl)benzoate were introduced into 20 ml of N,N-dimethylformamide and then admixed with 758 mg (95% by weight; 10.3 mmol) of sodium thiomethoxide. The mixture was stirred at RT for 2 hours and then freed from the solvent. The residue was taken up in ethyl acetate and water, the aqueous phase was extracted twice with ethyl acetate, and, finally, the combined organic phases were dried and freed from the solvent. The residue was purified by chromatography, giving 1.28 g of clean product.

Workup

  1. extractionwater, the aqueous phase was extracted twice with ethyl acetate
  2. customfinally, the combined organic phases were dried
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-cf64531ad986452cbe6b030f12fe3a02
Source dataset
uspto-grants-2013_09
Patent number
US08536097B2

Reaction notes

Loading…