Malononitrile → HCID 131730706, compound

HRID 449150Notes

Reaction equation

HRID 449150 reaction equation
C(#N)CC#N.[H-].[Na+].Br[C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[C:12](C)(C)[C:11]=2[SiH:10]=1.BrBr.O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[SiH:10]1[C:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[CH:21][CH:9]=1

Participants

8

Reactant 4

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 86741833Bromine hydrateHCID 178421823HCID 178421823, compound

Product 1

HCID 131730706HCID 131730706, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

in ice bath, 3.14 g of malononitrile was added to the suspension of 2.45 g of sodium hydride (60% in oil solution) in 50 mL of ethylene glycol dimethyl ether, then the mixture was warmed to room temperature, stirred for 20 minutes and 3.68 g of 2,7-dibromo-9,9-dimethyl silafluorene and 0.54 g of PdCl2(PPh3)2 were added. The mixture was heated to 120° C. for 12 hours, cooled to 0° C., and saturated Br2/H2O solution was added. A water was added, and the resulting mixture was vacuum filtered, washed with water, dried, and column chromatographed to give the product. MALDI-TOF-MS (m/z): 336.4 (M+).

Workup

  1. temperatureThe mixture was heated to 120° C. for 12 hours
  2. temperaturecooled to 0° C.
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customcolumn chromatographed
  7. customto give the product

Sources & evidence

ORD record
ord-f2e37666bee24a05806d8d5d7233e405
Source dataset
uspto-grants-2013_07
Patent number
US08481754B2

Reaction notes

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