Iodine → 2,2-Diphenyl-1-(diisopropylphosphino)-1-methylcyclopropane

HRID 1247701

Reaktionsgleichung

Reaktionsgleichung von HRID 1247701
Br[CH:2]1[CH2:4][C:3]1([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Mg].II.Cl[P:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23].[CH3:28]CCCCC>[Cu](I)I.C1COCC1>[C:5]1([C:3]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:4][C:2]2([P:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH3:28])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

8

Edukt 5

HCID 807IodineHCID 8058HexaneHCID 282328(2-Bromo-1-phenylcyclopropyl)benzeneHCID 538967ChlorodiisopropylphosphineHCID 5462224Magnesium

Produkt 1

HCID 219091352,2-Diphenyl-1-(diisopropylphosphino)-1-methylcyclopropaneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 1-bromo-2,2-diphenylcyclopropane (1.43 g, 5.0 mmol), magnesium (0.133 g, 5.5 mmol) and THF (10 ml) were placed in a reaction flask, followed by addition of a trace amount of iodine and stirring at 40° C. for 1.5 hours. After cooling, copper iodide (0.952 g, 5.0 mmol) and chlorodiisopropylphosphine (0.80 ml, 5.0 mmol) were added and the resulting mixture was stirred at 40° C. for 5 hours, followed by cooling to room temperature. The resulting mixture was diluted with hexane (20 ml) and crystal separated was collected by filtration. The crystal was dissolved in toluene, and the toluene solution was washed with a 28% aqueous ammonia and a brine, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure to give the title compound (1.06 g, 66%) as white crystal.

Aufarbeitung

  1. temperatureAfter cooling
  2. stirringthe resulting mixture was stirred at 40° C. for 5 hours
  3. temperatureby cooling to room temperature
  4. customseparated
  5. filtrationwas collected by filtration
  6. dissolutionThe crystal was dissolved in toluene
  7. washthe toluene solution was washed with a 28% aqueous ammonia
  8. dry with materiala brine, and dried over anhydrous magnesium sulfate
  9. customThen, the solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c365289a83e448169295659bb3949063
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129367B2

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