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

HRID 1429320Notes

Reaction equation

HRID 1429320 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

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 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-51ba368cc96645efa9c34e195be19a03
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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