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

HRID 1431034
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HRID 1431034 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

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 2M sodium carbonate aqueous solution were combined under argon atmosphere, and the mixture was stirred at 85° C. for 8 hours and left standing overnight. Water was added to the reaction mixture, and the mixture was stirred at room temperature for one hour. The mixture was filtered, the filtrate was extracted with toluene, and the organic phase was washed with water and subsequently with a saturated saline solution. The liquid was dried on sodium sulfate, and then toluene was removed by distillation under reduced pressure. A brown oily substance which resulted was refined by silica gel chromatography to obtain 11.8 g (yield: 42.4%) of 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene.

후처리

  1. waitleft
  2. waitstanding overnight
  3. stirringthe mixture was stirred at room temperature for one hour
  4. filtrationThe mixture was filtered
  5. extractionthe filtrate was extracted with toluene
  6. washthe organic phase was washed with water and subsequently with a saturated saline solution
  7. customThe liquid was dried on sodium sulfate
  8. customtoluene was removed by distillation under reduced pressure
  9. customA brown oily substance which resulted

출처 및 근거

ORD 기록
ord-97a6189f1b0e4066a1142afc163e968b
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08941099B2

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