Ethyl bromoacetate → Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetate

HRID 2247310Notes

Reaction equation

HRID 2247310 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC(C)=O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 3742252Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-mercaptophenol in dry acetone was treated successively with excess of potassium carbonate and ethyl bromoacetate. The reaction mixture was refluxed overnight. After allowing the reaction mixture to cool to rt, it was filtered through celite and washed with acetone. The filtrate was concentrated and the residue was partitioned between water and EtOAc. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated in-vacuo. The residue was purified by flash chromatography (silica, hexanes:ether, 3:1 to 1:1) to provide the desired thioether.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationit was filtered through celite
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between water and EtOAc
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in-vacuo
  10. customThe residue was purified by flash chromatography (silica, hexanes:ether, 3:1 to 1:1)

Sources & evidence

ORD record
ord-bb8691d3adbb4604867ff42f62951372
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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