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Sodium Hydroxide → 9-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

HRID 42384
ノート
印刷プレビュー

反応式

HRID 42384 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.[OH-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][C:25]=2[CH:24]=1>CS(C)=O>[C:25]12[CH2:26][CH2:27][C:28]=1[CH:29]=[CH:30][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][C:5]1([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[C:25]4[C:28](=[CH:29][CH:30]=3)[CH2:27][CH2:26]4)[C:4]3[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=3[C:11]3[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)=[CH:24]2
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

5

反応物 3

HCID 14798Sodium HydroxideHCID 1400732,7-DibromofluoreneHCID 580284923-(4-Bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene

生成物 1

HCID 580284989-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

To an oven-dried three-neck round-bottom flask under nitrogen, were added 25.97 g of 2,7-dibromofluorene, 32.06 g sodium hydroxide, 1.33 g KI, and 300 mL anhydrous DMSO. The 46 g 3-(4-bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene 300 mL anhydrous DMSO was added via cannula. The reaction was heated to 80° C. After 4 hours, the reaction was quenched by the addition of DI water (10 mL). The excess salt was removed by filtration. 500 mL Ethyl acetate was added, and extracted with DI water (3×300 mL) and brine (3×300 mL). The combined organic layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the solvent was removed by rotary evaporation. The product (43 g) was purified by flash chromatography using hexane. The structure was confirmed by NMR.

後処理

  1. customthe reaction was quenched by the addition of DI water (10 mL)
  2. customThe excess salt was removed by filtration
  3. addition500 mL Ethyl acetate was added
  4. extractionextracted with DI water (3×300 mL) and brine (3×300 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. customMagnesium sulfate was removed by filtration
  7. customthe solvent was removed by rotary evaporation
  8. customThe product (43 g) was purified by flash chromatography

出典と根拠

ORDレコード
ord-eef2893e491a4d5ab05d9efdcf8e0d14
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08535974B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート