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

HRID 1431034
Notes
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Reaction equation

HRID 1431034 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-97a6189f1b0e4066a1142afc163e968b
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08941099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes