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1,6-Dibromohexane → 2,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene

HRID 514168
ノート
印刷プレビュー

反応式

HRID 514168 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.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[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)[C:5]([CH2:10][CH2:11][CH2:12][CH2:4][CH2:3][CH2:2][Br:1])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23])[C:4]=2[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 123681,6-DibromohexaneHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

生成物 1

HCID 218679302,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene収率 56.5%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344
Dichloromethane
溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1 (5.0 g, 15.43 mmol), 1,6-dibromohexane (30 mL), tetrabutylammonium bromide (TBAB) (0.5 g), and potassium hydroxide aqueous solution (30 mL, 50% w/w) was stirred at 70° C. for 24 h under nitrogen. After diluting the reaction mixture with dichloromethane, the organic layer was washed with water and brine. The separated organic layer was dried over magnesium sulfate, and dichloromethane was evaporated. The residual 1,6-dibromohexane was distilled in a vacuum, and compound 2 (5.67 g, 56.5%) was obtained as a white crystal by chromatography with hexane/CH2Cl2 (95:5) as the eluent; m.p. 68° C. 1H NMR (500 MHz, CDCl3). δ (ppm): 7.51 (d, 2H, J=8.0 Hz), 7.45 (d, 2H, J=8.0 Hz), 7.42 (s, 2H), 3.27 (t, 4H, J=7 Hz), 1.91 (t, 4H, J=8.5 Hz), 1.65 (p, 4H, J=8 Hz), 1.18 (p, 4H, J=8 Hz), 1.06 (p, 4H, J=7.5 Hz), 0.57 (m, 4H).

後処理

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe separated organic layer was dried over magnesium sulfate, and dichloromethane
  3. customwas evaporated
  4. distillationThe residual 1,6-dibromohexane was distilled in a vacuum

出典と根拠

ORDレコード
ord-0a2e70d02b8142bc9d4e1b53a944a2c9
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09105851B2

反応ノート

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