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1,1-Dibromoethane → Tributyl-(4-ethylphenyl)stannane

HRID 221111
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인쇄 미리보기

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HRID 221111 반응식
[Mg].BrC(Br)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18].[F-].[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=1)[CH2:25][CH2:26][CH3:27]
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참가 물질

8

반응물 5

HCID 112011,1-DibromoethaneHCID 15096Tributyltin ChlorideHCID 153131-Bromo-4-ethylbenzeneHCID 522689Potassium FluorideHCID 5462224Magnesium

생성물 1

HCID 60041267Tributyl-(4-ethylphenyl)stannane수율 92.9%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of magnesium (896 mg) in tetrahydrofuran (20 ml) was added dibromoethan (0.1 ml), and the mixture was stirred at room temperature for 15 minutes. Thereto was added dropwise a solution of 1-bromo-4-ethylbenzene (5.7 g) in tetrahydrofuran (20 ml), and subsequently, the mixture was stirred at room temperature for one hour. The reaction mixture was cooled to −78° C., and thereto was added dropwise tributyltin chloride (9.49 g). The mixture was stirred at the same temperature for 30 minutes, and then at room temperature for one hour. To the reaction mixture were added 10% aqueous potassium fluoride solution and ethyl acetate, and the mixture was stirred at room temperature for 30 minutes. Insoluble materials were filtered off. The organic layer of the filtrate was washed with water and brine successively, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by alumina column chromatography (hexane) to give the desired tri-n-butyl(4-ethylphenyl)tin (10.7 g) as colorless oil. EI-Mass m/Z 337 (M-Bu).

후처리

  1. stirringsubsequently, the mixture was stirred at room temperature for one hour
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. stirringThe mixture was stirred at the same temperature for 30 minutes
  4. waitat room temperature for one hour
  5. stirringthe mixture was stirred at room temperature for 30 minutes
  6. filtrationInsoluble materials were filtered off
  7. washThe organic layer of the filtrate was washed with water and brine successively
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by alumina column chromatography (hexane)

출처 및 근거

ORD 기록
ord-8fc2004b953e4e50b62929aa4fd2ac9a
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202984B2

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