Hydrochloric Acid → m-Bromophenyl 3-methyl-2-butenyl sulfide

HRID 899274Notes

Reaction equation

HRID 899274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]([CH3:20])=[CH:17][CH2:18]Br.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:18][CH:17]=[C:16]([CH3:20])[CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 80597m-Bromobenzenethiol

Product 1

HCID 22640690m-Bromophenyl 3-methyl-2-butenyl sulfide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromothiophenol (5.0 g) in 60 mL of DMF was treated with 3.75 g of ground potassium carbonate and 3.2 mL of 3,3-dimethylallyl bromide. The reaction mixture was stirred at room temperature for two hours, poured onto 75 mL of ice-water, acidified to pH 2.0 with 10% HCl and extracted with three 75 mL portions of ether. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by short path distillation (T=170° C. at 950 mTorr) to give 5.651 g of 1-bromo-3-(3-methyl-but-2-enylsulfanyl)-benzene as a colorless liquid.

Workup

  1. extractionextracted with three 75 mL portions of ether
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. distillationThe product was purified by short path distillation (T=170° C. at 950 mTorr)

Sources & evidence

ORD record
ord-707df612164e4f529073e39112236676
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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