1,2-Dibromoethane → 2-(2-Bromoethylthio)-thiophene

HRID 2279337Notes

Reaction equation

HRID 2279337 reaction equation
C(=O)([O-])[O-].[K+].[K+].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[SH:12].[Br:13][CH2:14][CH2:15]Br>>[Br:13][CH2:14][CH2:15][S:12][C:8]1[S:7][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 5226742-Thiophenethiol

Product 1

HCID 122011192-(2-Bromoethylthio)-thiopheneYield 95%

Conditions

Temperature
78 °C

Procedure

Potassium carbonate (2.50 g, 18.07 mmol, 2.1 eq) is added at room temperature to a stirred solution of thiophene-2-thiol (813 μL, 8.61 mmol, 1.0 eq) in 1,2-dibromoethane (10 mL) and the resulting mixture is stirred at 78° C. for 3 hours. Then potassium carbonate is removed by filtration and the mother liquid is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: cyclohexane 100%) to afford 2-(2-bromo-ethylsulfanyl)-thiophene as a light yellow oil (1.86 g, 95% yield).

Workup

  1. customThen potassium carbonate is removed by filtration
  2. concentrationthe mother liquid is concentrated
  3. customto give a crude that
  4. customis purified by column chromatography (silica gel, eluent: cyclohexane 100%)

Sources & evidence

ORD record
ord-459e5de513294e409d99b17c4cd175b4
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

Loading…