Sodium Iodide → (1-Bromovinyl)trimethylsilane

HRID 2253511Notes

Reaction equation

HRID 2253511 reaction equation
[Na+].[I-:2].CN[C@@H]1CCCC[C@H]1NC.[Br:13][C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH2:15].CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I.ClCCl.C1COCC1>[Br:13][C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH2:15].[I:2][C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH2:15]

Participants

10

Reactant 4

HCID 5238Sodium IodideHCID 8182DodecaneHCID 83660(1-Bromovinyl)trimethylsilaneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 2

HCID 83660(1-Bromovinyl)trimethylsilaneHCID 14175464HCID 14175464, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 1-bromo-1-(trimethylsilyl)ethylene (155 μL, 1.00 mmol), and THF (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 70° C. for 15 h. The resulting suspension was allowed to reach room temperature. Dichloromethane (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 95% conversion of 1-bromo-1-(trimethylsilyl)ethylene and clean formation of 1-iodo-1-(trimethylsilyl)ethylene.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Sources & evidence

ORD record
ord-e65fbe887f17419fa401f11e7c226571
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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