Potassium Carbonate → HCID 22723477, 화합물

HRID 1581872노트

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HRID 1581872 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](I)=[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([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+].COCCOCCN(CCOCCOC)CCOCCOC>[Cu]>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([C:11]3[CH:10]=[CH:9][C:8]([N:42]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:7][C:6]=3[C:5]2([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])=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 227234762-Bromo-9,9-didecyl-7-iodo-9H-fluorene

생성물 1

HCID 22723477HCID 22723477, 화합물수율 61%

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

A mixture of 2-bromo-7-iodo-9,9-didecylfluorene (52.13 g, 0.08 mol), diphenylamine (15.6 g, 0.0922 mol, 1.152 eq), potassium carbonate (25.5 g, 0.1844 mol), TDA-1 (5 mL), copper bronze (3.0 g, 0.05 g atom) and xylenes (75 mL) was brought to reflux, and 35 ml, of xylenes were distilled off to reach a reaction temperature of 160° C. The reaction was maintained at this temperature for 18 hours. Some more solvent was distilled off to reach a reaction temperature of 175° C., where the reaction was held for additional 6 hours. The mixture was then cooled, diluted with 100 mL toluene, filtered, the filtrate was concentrated, and the residue was transferred to a column of 600 g of silica gel. Elution with 750 mL hexanes returned a mixture of dibromo and bromoiodo fluorenes as an oil, 10.3 g. Elution with heptane-toluene, 1:1 gave the product, 33.48 g (61% yield, 77% yield on consumed bromoiodo fluorene), m.p. 66.8-69.2° C. Mass Spec. (m/z): 691, 693 (M+).

후처리

  1. temperatureto reflux
  2. distillation35 ml, of xylenes were distilled off
  3. customa reaction temperature of 160° C
  4. temperatureThe reaction was maintained at this temperature for 18 hours
  5. distillationSome more solvent was distilled off
  6. customa reaction temperature of 175° C., where
  7. temperatureThe mixture was then cooled
  8. additiondiluted with 100 mL toluene
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated
  11. washElution with 750 mL hexanes
  12. additiona mixture of dibromo and bromoiodo fluorenes as an oil, 10.3 g
  13. washElution with heptane-toluene, 1:1
  14. customgave
  15. customthe product, 33.48 g (61% yield, 77% yield on consumed bromoiodo fluorene), m.p. 66.8-69.2° C

출처 및 근거

ORD 기록
ord-59f1469fe8eb434bb1f6e2cbb8b3be03
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730793B1

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