1-Chloro-4-nitrobenzene → Trimethyl((4-nitrophenyl)ethynyl)silane

HRID 857838Notes

Reaction equation

HRID 857838 reaction equation
C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCCCC.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30].Cl[C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1>C(NCC)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:41]([C:38]1[CH:39]=[CH:40][C:35]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[CH:36][CH:37]=1)([O-:43])=[O:42]

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 66111TrimethylsilylacetyleneHCID 58194762Hexyldiadamantyl-phosphine

Product 1

HCID 4296099Trimethyl((4-nitrophenyl)ethynyl)silaneYield 89%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8021DiethylamineSolvent

Procedure

0.005 mol % of Pd(OAc)2, 0.01 mol % of hexyldiadamantyl-phosphine and 1 mol % of Cu(I)I are added to a mixture of 12 mmol of trimethylsilylacetylene and 10 mmol of 4-chloronitrobenzene in 40 ml of diethylamine. The mixture is stirred under reflux until conversion is complete. The readily volatile constituents are then removed under vacuum. The residue is dissolved in toluene and washed with water. After chromatography on silica gel, 89% of 1-(4-nitrophenyl)-2-trimethylsilylacetylene is obtained.

Workup

  1. temperatureunder reflux until conversion
  2. customThe readily volatile constituents are then removed under vacuum
  3. dissolutionThe residue is dissolved in toluene
  4. washwashed with water

Sources & evidence

ORD record
ord-5add0013c2ac4190ae1f72706995d86a
Source dataset
uspto-grants-2006_12
Patent number
US07148176B2

Reaction notes

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