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

HRID 1247701

反応式

HRID 1247701 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.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

参加物

8

反応物 5

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

生成物 1

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

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-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.

後処理

  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

出典と根拠

ORDレコード
ord-c365289a83e448169295659bb3949063
出典データセット
uspto-grants-2006_10
特許番号
US07129367B2

関連ノート

読み込み中…