4-Bromothiophenol → [(4-Bromophenyl)thio]tris(1-methylethyl)silane

HRID 1872022Notes

Reaction equation

HRID 1872022 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH:9]([Si:12](Cl)([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].N12CCCN=C1CCCCC2>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][Si:12]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 660494-BromothiophenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139400Triisopropylsilyl chloride

Product 1

HCID 11484753[(4-Bromophenyl)thio]tris(1-methylethyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 45 grams of 4-bromothiophenol in 250 mL of THF was added 53 mL of triisopropylsilyl chloride and 38 mL of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under a nitrogen atmosphere. The reaction mixture heated spontaneously to reflux. The reaction mixture was allowed to cool and was diluted with 500 mL of hexanes. The resultant white suspension was filtered through a pad of Celite® (diatomaceous earth), and the filter cake was washed with additional hexanes and 100 mL of ether. The filtrate was washed with ice-cold 0.1 N aqueous HCl, water, aqueous NaHCO3, and saturated aqueous NaCl, dried over MgSO4, and concentrated under vacuum to obtain 82 grams of the title compound of Step A as a clear oil. 1H NMR (CDCl3, 300 MHz) δ 1.1 (m, 18H), 1.2 (m, 3H), 7.3-7.4 (m, 4H).

Workup

  1. temperatureThe reaction mixture heated spontaneously
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationThe resultant white suspension was filtered through a pad of Celite® (diatomaceous earth)
  5. washthe filter cake was washed with additional hexanes and 100 mL of ether
  6. washThe filtrate was washed with ice-cold 0.1 N aqueous HCl, water, aqueous NaHCO3, and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ad8ae9a4ac3b44ff8e92dc688f6580b8
Source dataset
uspto-grants-2000_08
Patent number
US06107319

Reaction notes

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