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Benzene, 1-bromo-3-ethyl- → 3-Ethylstyrene

HRID 397724
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HRID 397724 반응식
BrC1C=CC=C(CC)C=1.[CH2:10]([C:14]([Sn])=[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18]C)CCC>CN(C)C=O>[CH2:22]([C:21]1[CH:20]=[C:15]([CH:14]=[CH2:10])[CH:16]=[CH:17][CH:18]=1)[CH3:23]
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참가 물질

4

반응물 2

HCID 123170Benzene, 1-bromo-3-ethyl-HCID 53438229Tri(butyl)vinyltin

생성물 1

HCID 241433-Ethylstyrene수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a solution of 1-bromo-3-ethylbenzene (2.0 g, 10.8 mmol) in deoxygenated N,N-dimethylformamide (50 ml) under nitrogen was added tributylvinyltin (5.0 g, 16.2 mmol) and tetrakistriphenylphosphine palladium (0) (500 mg, 4 mol %) and the reaction mixture was heated to 75° C. for 7 h. The cooled reaction mixture was poured onto water (400 ml) and extracted with diethyl ether (5×200 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. This was distilled under reduced pressure to afford a residue that was partitioned between water and hexane. The layers were separated and the aqueous layer was extracted with hexane. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (1.4 g, 98%).

후처리

  1. customThe cooled reaction mixture
  2. additionwas poured onto water (400 ml)
  3. extractionextracted with diethyl ether (5×200 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product
  8. distillationThis was distilled under reduced pressure
  9. customto afford a residue that
  10. customwas partitioned between water and hexane
  11. customThe layers were separated
  12. extractionthe aqueous layer was extracted with hexane
  13. dry with materialThe combined extracts were dried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ce80f71b5d28447cbc00cf4d9786e3a5
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610711B2

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