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

HRID 1282454
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HRID 1282454 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매

3
HCID 24014Cupric Chloride촉매HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a863d69d3db4422399910c6a7a8a89b5
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06455720B1

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