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Ethanol → 1-(5-Methoxybiphenyl-2-yl)pyrene

HRID 1852554
ノート
印刷プレビュー

反応式

HRID 1852554 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1(B(O)O)[C:29]2[C:30]3=[C:31]4[C:26](=[CH:27][CH:28]=2)[CH:25]=[CH:24][CH:23]=[C:22]4[CH:21]=[CH:20][C:19]3=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2[C:22]3[C:31]4=[C:30]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:29]5[CH:28]=[CH:27][C:26]4=[CH:25][CH:24]=2)=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=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

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5084102Pyren-1-ylboronic acidHCID 675132132-Bromo-5-methoxy-1,1'-biphenyl

生成物 1

HCID 867236161-(5-Methoxybiphenyl-2-yl)pyrene収率 76.1%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 11.1 g (42.4 mmol) of 2-bromo-5-methoxybiphenyl, 10.43 g (42.4 mmol) of pyren-1-ylboronic acid, 0.5 g (0.424 mmol) of tetrakis(triphenylphosphine)palladium, 32 ml of 2M Na2CO3, 80 ml of EtOH and 160 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 12.4 g (76%) as a white solid.

後処理

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe organic layer was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

出典と根拠

ORDレコード
ord-b05b47b058f74bc1a91a73e0fd66bb4d
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962160B2

反応ノート

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