Diethyl Ether → HCID 53939773, compound

HRID 266579Notes

Reaction equation

HRID 266579 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](F)[C:3]=1[C:13]([CH3:15])=[CH2:14].[CH3:16][S-:17].[Na+].CCOCC>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:17][CH3:16])[C:3]=1[C:13]([CH3:15])=[CH2:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 53781233HCID 53781233, compound

Product 1

HCID 53939773HCID 53939773, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-chloro-2-fluoro-3-isopropenylbenzoate (8.6 g) and sodium thiomethoxide (3.15 g) in dimethyl formamide was heated at 50° C. for 3 hours and stirred at room temperature overnight. Ether was added and the mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and hexane to give methyl 4-chloro-3-isopropenyl-2-(methylsulphenyl)benzoate (5.95 g) as a clear oil NMR (CDCl3) 2.1(s,3H), 2.35(s,3H), 3.95(s,3H), 4.9(s, 1H), 5.4(s, 1H), 7.45(s,2H).

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography
  6. washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-50b032e113874cf380706b37620cefec
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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