tert-Butyl bromoacetate → Tert-butyl (methylthio)acetate

HRID 2253977Notes

Reaction equation

HRID 2253977 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][SH:11].[Na]>>[CH3:10][S:11][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 45051789Methylmercaptan sodium

Product 1

HCID 10241116Tert-butyl (methylthio)acetateYield 96.5%

Procedure

Under ice cooling, 33.4 g of tert-butyl bromoacetate was gradually added to 80.0 g of 15% sodium methylmercaptan aqueous solution and the resulting mixture was reacted at room temperature overnight. After completion of the reaction, the reaction mixture was extracted 4 times with ethyl acetate and the extract was washed with saturated sodium chloride aqueous solution. After the ethyl acetate layer was dried over magnesium sulfate, ethyl acetate was distilled off to give 26.8 g of crude tert-butyl (methylthio)acetate.

Workup

  1. customthe resulting mixture was reacted at room temperature overnight
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted 4 times with ethyl acetate
  4. washthe extract was washed with saturated sodium chloride aqueous solution
  5. dry with materialAfter the ethyl acetate layer was dried over magnesium sulfate, ethyl acetate
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-615ec9bb67ae47e998ccd34723eb8455
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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