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

HRID 1247702

反応式

HRID 1247702 の反応式
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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aec168b5a6f641b3bf59928e3e57392e
出典データセット
uspto-grants-2006_10
特許番号
US07129367B2

関連ノート

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