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

HRID 1374529Notes

Reaction equation

HRID 1374529 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-781188160e044d48aaca46d9fc7d06cb
Source dataset
uspto-grants-2007_01
Patent number
US07166586B2

Reaction notes

Loading…