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

HRID 2415187Notes

Reaction equation

HRID 2415187 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-e89eb26c8e334a1d9eee1305dca76086
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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