Iodine → Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphane

HRID 1247702

반응식

HRID 1247702 반응식
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.[Br-].[Li+].Cl[P:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:24]([CH3:27])([CH3:26])[CH3:25].[CH3:32]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:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:32])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

9

반응물 6

HCID 807IodineHCID 8058HexaneHCID 82050Lithium BromideHCID 139566Di-tert-butylchlorophosphineHCID 282328(2-Bromo-1-phenylcyclopropyl)benzeneHCID 5462224Magnesium

생성물 1

HCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphane수율 47%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

Under a nitrogen atmosphere, 1-bromo-2,2-diphenyl-cyclopropane (1.44 g, 5.0 mmol), magnesium (0.134 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 one hour. After cooling, copper iodide (0.962 g, 5.0 mmol), lithium bromide (0.567 g, 6.5 mmol) and chlorodi-tert-butylphosphine (0.95 ml, 5.0 mmol) were added and the resulting mixture was stirred at 60° C. for 3 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. The solvent was then removed under reduced pressure to give the title compound (0.83 g, 47%) as white crystal.

후처리

  1. temperatureAfter cooling
  2. stirringthe resulting mixture was stirred at 60° C. for 3 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. customThe solvent was then removed under reduced pressure

출처 및 근거

ORD 기록
ord-aec168b5a6f641b3bf59928e3e57392e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129367B2

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