Sodium Iodide → Bis(diphenylphosphine)methane monooxide

HRID 581452

반응식

HRID 581452 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([P:7]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:8][P:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.BrCCBr.[OH-:32].[Na+].[Na+].[I-]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[P:7]([CH2:8][P:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:32])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 74952Bis(diphenylphosphino)methane

생성물 1

HCID 303894Bis(diphenylphosphine)methane monooxide

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of palladium acetate (5 mg; 2.2×10-2 mmol), dppm (2.00 g; 5.21 mmol), 1,2-dibromoethane (2.0 g; 10.64 mmol), and dichloromethane (10 mL) was stirred for 20 minutes. To this solution, aqueous NaOH (20% by weight; 6 mL) containing NaI (40 mg; 0.27 mmol) was added and the mixture was vigorously stirred under reflux for 4 hours. The organic phase was filtered through a silica plug which was then washed with CH2Cl2 /AcOEt (3:1 by volume). The combined organic solutions were evaporated to dryness. The solid residue was dissolved in the minimum amount of boiling CH2Cl2, the warm solution was treated with ether (100 mL; portionwise) and left at room temperature for 2 hours. Slightly yellowish fluffy needles of spectroscopically and TLC pure dppmO were separated, washed with ether, and dried under vacuum. The yield was 1.53 g (74%). 1H NMR (CDCl3, 20° C.), δ: 3.1 (d, 2H, J=12.7 Hz, CH2); 7.1-7.9 (m, 20H, Ph). 31P NMR (CDCl3, 20° C.), δ: -26.5 (d, 1P, JP-P =50.5 Hz, PPh2); 29.8 (d, 1P, JP-P =50.5 Hz, P(O)Ph2).

후처리

  1. additionwas added
  2. stirringthe mixture was vigorously stirred
  3. temperatureunder reflux for 4 hours
  4. filtrationThe organic phase was filtered through a silica plug which
  5. washwas then washed with CH2Cl2 /AcOEt (3:1 by volume)
  6. customThe combined organic solutions were evaporated to dryness
  7. dissolutionThe solid residue was dissolved in the minimum amount of boiling CH2Cl2
  8. additionthe warm solution was treated with ether (100 mL
  9. waitportionwise) and left at room temperature for 2 hours
  10. customSlightly yellowish fluffy needles of spectroscopically and TLC pure dppmO were separated
  11. washwashed with ether
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-789bcb6607c249288db7e3cad7ad98e8
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919984

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