Potassium Carbonate → 1-Bromo-3-[(2,2-dimethoxyethyl)sulfanyl]benzene

HRID 1267844Notes

Reaction equation

HRID 1267844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:12][CH:11]([O:14][CH3:15])[O:10][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80597m-BromobenzenethiolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 185424641-Bromo-3-[(2,2-dimethoxyethyl)sulfanyl]benzeneYield 102.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Part A: A suspension of 3-bromothiophenol (15.2 g, 81 mmol), bromoacetaldehyde dimethylacetal (9.5 mL, 81 mmol) and potassium carbonate (12.2 g, 88 mmol) in acetone (90 mL) was stirred at ambient temperature overnight. The solid was filtered and rinsed with ether. Evaporation of the filtrate afforded 23 g of 1-bromo-3-((2,2-dimethoxyethyl)thio)benzene which was carried forward without further purification.

Workup

  1. filtrationThe solid was filtered
  2. washrinsed with ether
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-f42f293fcfc84996957ad9147071e3fc
Source dataset
uspto-grants-2003_04
Patent number
US06555542B1

Reaction notes

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