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

HRID 1247700

反応式

HRID 1247700 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]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:34]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]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:34])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

8

反応物 5

HCID 807IodineHCID 8058HexaneHCID 66180ChlorodiphenylphosphineHCID 282328(2-Bromo-1-phenylcyclopropyl)benzeneHCID 5462224Magnesium

生成物 1

HCID 219091302,2-Diphenyl-1-(diphenylphosphino)-1-methylcyclopropane収率 50%

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 (1.44 g, 5.0 mmol) and magnesium (0.134 g, 5.5 mmol) and THF (10 ml) were placed in a reaction flask. Then, a trace amount of iodine was added and the mixture was stirred at 40° C. for 2 hours. After cooling, copper iodide (0.961 g, 5.0 mmol) and chlorodiphenylphosphine (0.90 ml, 5.0 mmol) were added and the resulting mixture was stirred at 40° C. for 20 hours. After cooling to room temperature, hexane (10 ml) was added to the reaction mixture, and crystal separated was then collected by filtration. The crystal was dissolved in toluene, washed with an aqueous 28% ammonia solution and a brine, and dried over anhydrous magnesium sulfate. The solvent was then removed under reduced pressure and the concentrate was recrystallized from a mixture of methanol and toluene to give the title compound (0.98 g, 50%) as white crystal.

後処理

  1. temperatureAfter cooling
  2. stirringthe resulting mixture was stirred at 40° C. for 20 hours
  3. temperatureAfter cooling to room temperature
  4. customseparated
  5. filtrationwas then collected by filtration
  6. dissolutionThe crystal was dissolved in toluene
  7. washwashed with an aqueous 28% ammonia solution
  8. dry with materiala brine, and dried over anhydrous magnesium sulfate
  9. customThe solvent was then removed under reduced pressure
  10. customthe concentrate was recrystallized from a mixture of methanol and toluene

出典と根拠

ORDレコード
ord-3d2a9b07df3147e3a5fcf8e9e22630ad
出典データセット
uspto-grants-2006_10
特許番号
US07129367B2

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