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

HRID 1870976Notes

Reaction equation

HRID 1870976 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Br:10])[CH3:2].[Mg].Br[C:13](=[CH2:19])[CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16].CCOCC>O1CCCC1.C1C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Br:10])[CH3:2].[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[CH2:19])[CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH3:2]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 4173130(2-Bromoallyl)trimethylsilaneHCID 5462224MagnesiumHCID 130827251-Bromo-2-(ethylsulfanyl)benzene

Product 2

HCID 130827251-Bromo-2-(ethylsulfanyl)benzeneHCID 536675682-(2-Ethylmercaptophenyl)allyl trimethylsilane

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of the Grignard reagent of 1-ethylmercapto-2-bromobenzene in tetrahydrofuran was prepared in the following way: 1.50 g (6.9 mmol) of 1-ethylmercapto-2-bromobenzene were added to 218 mg (9.0 mmol) of magnesium in 8 ml of anhydrous tetrahydrofuran at room temperature under N2 and It was heated at reflux for 1 h. Meanwhile, a solution of 1.20 g (6.2 mmol) of (2-bromoallyl)-trimethylsilane and 358 mg (0.31 mmol) of tetrakis(triphenylphosphine)-palladium in 6 ml of dry benzene was stirred at 80° C. under N2 for 30 min. Then it was cooled to 50° C. and to it was added the Grignard reagent described above. The reaction mixture was stirred at 40° C. for 3 h and was poured into 100 ml of ether. It was washed with water (20 ml×2), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with hexane to give [2-(2-ethylmercaptophenyl)allyl trimethylsilane as a colorless oil.

Workup

  1. temperatureIt was heated
  2. temperatureat reflux for 1 h
  3. washIt was washed with water (20 ml×2)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography with hexane

Sources & evidence

ORD record
ord-171de5d7d90248b6ae76605748427084
Source dataset
uspto-grants-2000_08
Patent number
US06100293

Reaction notes

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