1-Bromooctane → 2,7-Dibromo-9,9-di-n-octylfluorene

HRID 11743

반응식

HRID 11743 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH2:19]([C:5]1([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH3:10])[C:4]2[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

참가 물질

5

반응물 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 1400732,7-Dibromofluorene

생성물 1

HCID 52153212,7-Dibromo-9,9-di-n-octylfluorene수율 150.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of 28.5 g (88 mmol) 2,7-dibromofluorene in 800 mL THF was added 8.8 g (220 mmol) sodium hydride (60%) in several portions at room temperature. The mixture was heated at 60° C. and 43 g (220 mmol) bromooctane in 200 mL THF was added dropwisely into the mixture and refluxed overnight. The mixture was concentrated and diluted with water, and then extracted with diethyl ether. After washing with brine, the ether solution was dried over anhydrous MgSO4 and the ether was then removed by evaporation. This crude solid was purified by a silica chromography with hexane and recrystallized from ethanol to give white solid (36.3 g, yield 75.3%, mp. 52˜54° C.). 1H NMR (500 MHz, CDCl3), δ (ppm): 7.51 (2H, d), 7.44 (2H, d), 7.41 (2H, s), 1.89 (4H, m), 1.02˜1.20 (20H, m), 0.81 (6H, t), 0.56 (4H, m).

후처리

  1. temperaturerefluxed overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with diethyl ether
  5. washAfter washing with brine
  6. dry with materialthe ether solution was dried over anhydrous MgSO4
  7. customthe ether was then removed by evaporation
  8. customThis crude solid was purified by a silica chromography with hexane
  9. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-da03422107184f23b2816271e7ba8577
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098295B2

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