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

HRID 849449Notes

Reaction equation

HRID 849449 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 of abs. ethanol. The reaction mixture is refluxed for 20 hours. The solvent is then distilled off and the residue is taken up in methylene chloride and washed with water. The organic phase is dried over sodium sulfate and the solvent is removed. The useful product 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 useful product is purified by column chromatography

Sources & evidence

ORD record
ord-39251ff6549747feb1749397a8311eb4
Source dataset
uspto-grants-2000_01
Patent number
US06013607

Reaction notes

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