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

HRID 389026

Reaction equation

HRID 389026 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[SH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>CN(C=O)C>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([S:14][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 3742252Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetateYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl bromoacetate (21.5 mL, 194 mmol) and potassium carbonate (50.7 g, 367 mmol) were added to a DMF (450 mL) solution of 4-mercaptophenol (23.1 g, 183 mmol), and the mixture was stirred at room temperature overnight. The solvents were distilled off under a reduced pressure, water was added to the residue, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate, and solvents were distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), to give 30.3 g (78%) of the captioned compound.

Workup

  1. distillationThe solvents were distilled off under a reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate, and solvents
  6. distillationwere distilled off under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-924f471dc6914090b819658749ab2e6a
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Linked notes

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