Triethylamine → 1-(2-Trimethylsilyl-1-ethynyl)-3-(propylsulfonyl)benzene

HRID 2390140Notes

Reaction equation

HRID 2390140 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:3]=1.C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:21][Si:22]([CH3:24])([CH3:23])[C:25]#[C:26][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 565942651-Bromo-3-(propylsulfonyl)benzene2×

Product 1

HCID 565942661-(2-Trimethylsilyl-1-ethynyl)-3-(propylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-3-(propylsulfonyl)benzene (Intermediate 5; 23 g, 88 mmol) in THF (450 ml) was treated with Pd(dppf)Cl2 (3.9 g, 5.3 mmol), triethylamine (13.4 g, 132 mmol) and trimethylsilyl acetylene (8.64 g, 88 mmol). The reaction mixture was stirred at RT for 10 minutes, then cuprous iodide (1.0 g, 5.3 mmol) was added, the reaction mixture was heated at 60° C. for 24 h. The reaction mixture was filtered to remove the solid and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography using petroleum ether and ethyl acetate (98:2) as a eluent to afford the title compound as a brown oil.

Workup

  1. temperaturethe reaction mixture was heated at 60° C. for 24 h
  2. filtrationThe reaction mixture was filtered
  3. customto remove the solid
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-7b79e89589634bc78f5581f11d2d473b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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