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

HRID 11743

反応式

HRID 11743 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 52153212,7-Dibromo-9,9-di-n-octylfluorene収率 150.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-da03422107184f23b2816271e7ba8577
出典データセット
uspto-grants-2006_08
特許番号
US07098295B2

関連ノート

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