Ethyl 3-(2-bromoethoxy)-2-methylbenzoate → Ethyl 3-(2-methylsulfonylthioethoxy)-2-methylbenzoate

HRID 582822Notes

Reaction equation

HRID 582822 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:6]([CH3:16])=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:17][S:18]([O-:21])(=[S:20])=[O:19].[K+]>C(O)C>[CH3:17][S:18]([S:20][CH2:2][CH2:3][O:4][C:5]1[C:6]([CH3:16])=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:21])=[O:19]

Participants

4

Reactant 2

HCID 15376195Ethyl 3-(2-bromoethoxy)-2-methylbenzoateHCID 23696406Potassium thiomethanesulfonate

Product 1

HCID 15376196Ethyl 3-(2-methylsulfonylthioethoxy)-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 g (7 mmol) of ethyl 3-(2-bromoethoxy)-2-methylbenzoate and 1.1 g (7.3 mmol) of potassium thiomethanesulfonate are dissolved in 10 ml absolute ethanol. The reaction mixture is refluxed for 20 hours. The solvent is then distilled off and the residue taken up in methylene chloride and washed with water. The organic phase is dried over sodium sulfate and the solvent is removed. The product of value is purified by column chromatography.

Workup

  1. temperatureThe reaction mixture is refluxed for 20 hours
  2. distillationThe solvent is then distilled off
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe product of value is purified by column chromatography

Sources & evidence

ORD record
ord-971a12ba684246ea9e0f633a678e70d6
Source dataset
uspto-grants-1999_07
Patent number
US05925767

Reaction notes

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