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N-bromobutanimide → 2-Bromo-3-decyloxythiophene

HRID 41285
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HRID 41285 반응식
[CH2:1]([O:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:17][C:13]1[S:14][CH:15]=[CH:16][C:12]=1[O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 197606903-Decyloxythiophene

생성물 1

HCID 576532532-Bromo-3-decyloxythiophene수율 94%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

3-decyloxy-thiophene (5.50 g, 0.023 mol) was dissolved in CHCl3 (50 mL) under argon atmosphere. N-Bromosuccinimide (NBS) (4.09 g, 0.023 mol) was added to the solution as one portion. The mixture was reacted under argon and protected from light for 4˜8 hours at room temperature (25° C.). Afterwards it was distilled to remove CHCl3, allowed to cool to room temperature, and diluted with hexane (100 mL). The mixture was filtered and the filtrate was concentrated in vacuum. The residue was applied to silica gel, eluted with 1:9 ethyl acetate/hexane to give 6.97 g (94% yield) of light yellow liquid. Mw=319.30. Element Anal. Calcd. for C14H23BrOS: C, 52.66; H, 7.26; Br, 25.02; 0, 5.01; S, 10.04. Found: C, 52.62; H, 7.25; Br, 24.90; 0, 5.09; S, 10.04.

후처리

  1. customThe mixture was reacted under argon
  2. waitprotected from light for 4˜8 hours at room temperature
  3. custom(25° C.)
  4. distillationAfterwards it was distilled
  5. customto remove CHCl3
  6. additiondiluted with hexane (100 mL)
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated in vacuum
  9. washeluted with 1:9 ethyl acetate/hexane
  10. customto give 6.97 g (94% yield) of light yellow liquid

출처 및 근거

ORD 기록
ord-06c0e847b90741e2a045686a1e1c8f50
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530594B2

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