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4-Vinylpyridine → 4,4'-(9,9-Bis-n-decyl-2,7-fluorenediyldi-2,1-ethenediyl)bis-pyridine

HRID 342906
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HRID 342906 반응식
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[CH:3]=1.[C:36]1(C)[CH:41]=CC=C[C:37]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:58]([C:60]1[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=1)=[CH2:59].C([N:68]([CH2:71][CH3:72])[CH2:69][CH3:70])C>[Pd]>[CH2:26]([C:5]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]2[CH:7]=[C:8]([CH:59]=[CH:58][C:60]3[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=3)[CH:9]=[CH:10][C:11]=2[C:12]2[C:4]1=[CH:3][C:2]([CH:37]=[CH:36][C:41]1[CH:70]=[CH:69][N:68]=[CH:71][CH:72]=1)=[CH:14][CH:13]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 36612112,7-Dibromo-9,9-didecylfluorene

생성물 1

HCID 675756704,4'-(9,9-Bis-n-decyl-2,7-fluorenediyldi-2,1-ethenediyl)bis-pyridine수율 71.48%

시약·촉매·용매 1

HCID 23938
Palladium
촉매

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온도
95 °C

실험 절차

2,7-Dibromo-9,9-di-n-decyl-9H-fluorene (10.0 g, 16.5 mmol), tri-o-tolylphosphine (2.01 g, 6.6 mmol), degassed triethylamine (40 ml) and 4-vinylpyridine (5.35 ml, 49.62 mmol) was added to a single-necked round bottom flask under to nitrogen equipped with a magnetic stir bar and a reflux condenser. The palladium catalyst (0.19 g, 0.83 mmol) was added and the solution heated at 95° C. for 18 hours. The reaction mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was dissolved in methylene chloride, and the organic layer washed three times with equal volumes of water, dried over anhydrous MgSO4, filtered and concentrated. The product was purified by column chromotography on alumina using 30/70 ethyl acetate/hexane to yield the product as a yellow oil in 71.48% yield.Mass Spec. m/z 652 (M+), 511 (M--C10H21). Elemental Analysis: Calculated for C47H60N2 : C, 86.45, H, 9.26, N, 4.29. Found: C, 86.50, H, 8.84, N, 3.78.

후처리

  1. additionwas added to a single-necked round bottom flask under to nitrogen
  2. customequipped with a magnetic stir bar and a reflux condenser
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washthe organic layer washed three times with equal volumes of water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromotography on alumina using 30/70 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ed72695deaa241cba0ef112315c050f6
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05859251

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