Diethyl Ether → 1-Bromo-2-(ethylsulfanyl)benzene

HRID 1870975Notes

Reaction equation

HRID 1870975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH3:17].CCOCC>CN(C)C=O>[CH2:16]([S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 805982-Bromobenzenethiol

Product 1

HCID 130827251-Bromo-2-(ethylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a suspension of 1.00 g (5.3 mmol) of 2-bromo-benzenethiol and 1.47 g (10.6 mmol) of potassium carbonate in 15 ml of N,N-dimethylformamide was added 1.65 g (10.6 mmol) of iodoethane at 0° C. The reaction mixture was stirred at 55-60° C. for 12 h and was poured into 200 ml of ether. It was washed with water (20 ml×3), dried over MgSO4 and concentrated to afford 1-ethylsulfanyl-2-bromo-benzene as a colorless oil.

Workup

  1. washIt was washed with water (20 ml×3)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d97d6121b3b04074a21a0e516d16dce1
Source dataset
uspto-grants-2000_08
Patent number
US06100293

Reaction notes

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