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Iodine → Bis(1,1-dimethylethyl)(1-methyl-2,2-diphenylethenyl)phosphine

HRID 1282454
ノート
印刷プレビュー

反応式

HRID 1282454 の反応式
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:8](P(C2C=CC=CC=2)C2C=CC=CC=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].II.BrC1C=CC=CC=1.Cl[P:40]([C:45]([CH3:48])([CH3:47])[CH3:46])[C:41]([CH3:44])([CH3:43])[CH3:42]>[Cu](Cl)Cl.CCCCCCC.C1COCC1>[C:1]1([C:7]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:8]([P:40]([C:45]([CH3:48])([CH3:47])[CH3:46])[C:41]([CH3:44])([CH3:43])[CH3:42])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 807IodineHCID 7961BromobenzeneHCID 139566Di-tert-butylchlorophosphineHCID 5462224MagnesiumHCID 120108231,1-Diphenyl-2-(diphenylphosphino)propene

生成物 1

HCID 12010825Bis(1,1-dimethylethyl)(1-methyl-2,2-diphenylethenyl)phosphine収率 43.5%

試薬・触媒・溶媒

3
HCID 24014Cupric Chloride触媒HCID 8028Tetrahydrofuran溶媒HCID 8900Heptane溶媒

実験手順

Into a reactor were introduced 1.37 g (5.0 mmol) of the 2-bromo-11-diphenylpropene obtained in Example 1 (2), 0.134 g (5.5 mmol) of magnesium, and 11 mL of THF under a nitrogen atmosphere. Iodine and bromobenzene were added to the mixture in a slight amount to ascertain initiation of a reaction. Thereafter, the reaction mixture was refluxed for 2 hours and then cooled. Thereto were added 0.520 g (5.3 mmol) of copper chloride and 1.1 mL (5.5 mmol) of chlorodi-t-butylphosphine. This reaction mixture was refluxed for 18 hours and then cooled to room temperature. Thereto was added 14 mL of heptane. The crystals yielded were taken out by filtration and dissolved in 40 mL of ethyl acetate. The resultant solution was washed with 28% ammonia water and an aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol to obtain 0.736 g (43%) of the target compound as white crystals.

後処理

  1. custominitiation of a reaction
  2. temperatureThereafter, the reaction mixture was refluxed for 2 hours
  3. temperaturecooled
  4. temperatureThis reaction mixture was refluxed for 18 hours
  5. customThe crystals yielded
  6. filtrationwere taken out by filtration
  7. dissolutiondissolved in 40 mL of ethyl acetate
  8. washThe resultant solution was washed with 28% ammonia water
  9. dry with materialan aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
  10. customThereafter, the solvent was removed under reduced pressure
  11. customThe concentrate was recrystallized from ethanol

出典と根拠

ORDレコード
ord-a863d69d3db4422399910c6a7a8a89b5
出典データセット
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06455720B1

反応ノート

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