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

HRID 1247701Notes

Reaction equation

HRID 1247701 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c365289a83e448169295659bb3949063
Source dataset
uspto-grants-2006_10
Patent number
US07129367B2

Reaction notes

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