Ethanol → 12-(5-bromo-2-nitrophenyl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene

HRID 879915ノート

反応式

HRID 879915 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](I)[CH:3]=1.[CH3:12][C:13]1([CH3:47])[C:37]2[C:17]([CH:18]=[C:19]3[CH:36]=[C:35]4[C:22]([C:23]5[C:28]([C:29]6[C:34]4=[CH:33][CH:32]=[CH:31][CH:30]=6)=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:21][C:20]3=2)=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14]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.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:15]2[CH:16]=[C:17]3[C:37]([C:13]([CH3:47])([CH3:12])[CH:14]=2)=[C:20]2[C:19]([CH:36]=[C:35]4[C:22](=[CH:21]2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]4=2)=[CH:18]3)[CH:3]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 127002174-Bromo-2-iodo-1-nitrobenzeneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 8672250912-(5-bromo-2-nitrophenyl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene収率 57%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 7.5 g (22.8 mmol) of 4-bromo-2-iodo-1-nitrobenzene, 10.7 g (22.8 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium, 17 ml of 2M Na2CO3, 40 ml of EtOH and 100 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 7 g (yield 57%) of yellow product which was recrystallized from toluene.

後処理

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

出典と根拠

ORDレコード
ord-e68ef33c2b1c4b18b940d6d10491983e
出典データセット
uspto-grants-2015_03
特許番号
US08993130B2

反応ノート

読み込み中…