Hexane → 2-(2-nitrophenyl)thiophene

HRID 1983872ノート

反応式

HRID 1983872 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].CCCCCC>COCCOC.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>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([O-:18])=[O:17]

参加物

7

反応物 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 69115o-IodonitrobenzeneHCID 27339602-Thiopheneboronic acid

生成物 1

HCID 91672612-(2-nitrophenyl)thiophene収率 107.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

14.07 g (110 mmol) of 2-thiophene-boronic acid, 24.9 g (100 mmol) of 1-iodo-2-nitrobenzene, and 5.78 g (5 mmol) of tetrakis(triphenylphosphine)palladium(0) were dissolved in 250 ml of ethylene glycol dimethyl ether (DME), and 70 ml of 2M K2CO3 aqueous solution was added to the solution, and then the mixture was refluxed at 80° C. for 12 hours. After the reaction was completed, an organic layer was isolated and concentrated, and then isolated by column chromatography using hexane, thereby obtaining 22.1 g (yield: 98%) of 2-(2′-nitrophenyl)-thiophene (A′).

後処理

  1. customan organic layer was isolated
  2. concentrationconcentrated
  3. customisolated by column chromatography

出典と根拠

ORDレコード
ord-9694b2f7e6304b59a02c513545c1e0f3
出典データセット
uspto-grants-2009_06
特許番号
US07541736B2

反応ノート

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