Iodoethane → 1-Bromo-3-(ethylsulfanyl)benzene

HRID 1962765Notes

Reaction equation

HRID 1962765 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[CH:6]=[C:7]([SH:11])[CH:8]=[CH:9][CH:10]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Br:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][CH2:2][CH3:3])[CH:6]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

Product 1

HCID 130827271-Bromo-3-(ethylsulfanyl)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Iodoethane (0.46 mL, 0.0058 mol) was added to a suspension of 3-bromothiophenol (0.50 mL, 0.0048 mol), ACN (7.11 mL, 0.136 mol) and potassium carbonate (2.0 g, 0.014 mol). The reaction was stirred for 2 h at rt, was diluted with ethyl acetate and filtered to remove the solids. The reaction was concentrated in vacuo to give 1-bromo-3-(ethylthio)benzene as a colorless oil 1.0 gm, 100%

Workup

  1. filtrationfiltered
  2. customto remove the solids
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-2f66d21967f943b5af37949c2fb9b8ac
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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