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Toluene → 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene

HRID 1429320
ノート
印刷プレビュー

反応式

HRID 1429320 の反応式
[CH3:1][C:2]1([CH3:18])[C:14]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Br:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25](Br)[CH:26]=2)[CH:21]=1.C1(C)C=CC=CC=1.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.C(COC)OC>[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([C:12]1[CH:11]=[CH:10][C:9]3[C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2]([CH3:1])([CH3:18])[C:14]=3[CH:13]=1)[CH:24]=[CH:23]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

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 22348454(9,9-Dimethyl-9H-fluoren-2-yl)boronic acid

生成物 1

HCID 576484592-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene収率 42.4%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

In argon atmosphere, a mixture of 16.65 g (69.9 mmol) of 9,9-dimethyl-9H-fluorene-2-ylboronic acid, 20.0 g (69.9 mmol) of 2,6-dibromonaphthalene, 4.04 g (3.50 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 200 ml of dimethoxyethane, and 106 g of a 2 M sodium carbonate aqueous solution was stirred at 85° C. for 8 h and left standing overnight. After adding water, the mixture was stirred at room temperature for one hour. After filtration and extraction with toluene, the organic phase was washed with water and then with a saturated saline solution. After drying over sodium sulfate, the toluene was distilled off under reduced pressure. The obtained brown oily substance was purified by silica gel chromatography to obtain 11.84 g (yield: 42.4%) of 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene.

後処理

  1. waitleft
  2. waitstanding overnight
  3. stirringthe mixture was stirred at room temperature for one hour
  4. filtrationAfter filtration and extraction with toluene
  5. washthe organic phase was washed with water
  6. dry with materialAfter drying over sodium sulfate
  7. distillationthe toluene was distilled off under reduced pressure
  8. customThe obtained brown oily substance was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-51ba368cc96645efa9c34e195be19a03
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940412B2

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