1,2-Dimethoxyethane → 7-Bromo-2-(9-phenanthrenyl)naphthalene

HRID 1429328ノート

反応式

HRID 1429328 の反応式
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][C:23](Br)=[CH:24][CH:25]=2)[CH:20]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:20]=[C:21]2[C:26]([CH:25]=[CH:24][C:23]([C:12]3[C:11]4[C:6]([C:5]5[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=5[CH:13]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:22]2)=[CH:27][CH:28]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 6253552,7-DibromonaphthaleneHCID 117757049-Phenanthracenylboronic acid

生成物 1

HCID 575400157-Bromo-2-(9-phenanthrenyl)naphthalene収率 38.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

In argon atmosphere, a mixture of 18.64 g (83.9 mmol) of 9-phenanthreneboronic acid, 30.00 g (104.9 mmol) of 2,7-dibromonaphthalene, 4.85 g (4.2 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of dimethoxyethane, 200 ml of toluene, and 106 ml of a 2 M sodium carbonate was stirred at a bath temperature of 85° C. for 7 h. The reaction mixture was added with water and extracted with toluene. After washing with water, the organic phase was dried over magnesium sulfate. Then, the toluene was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 12.46 g (yield: 31.0%) of 7-bromo-2-(9-phenanthrenyl)naphthalene.

後処理

  1. extractionextracted with toluene
  2. washAfter washing with water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customThen, the toluene was removed by distillation under reduced pressure
  5. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-036d58eace664723946406ef9fdfad22
出典データセット
uspto-grants-2015_01
特許番号
US08940412B2

反応ノート

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