Toluene → 2-bromo-9,9-dimethyl-7-(naphthalene-2-yl)-9H-fluorene

HRID 1429318Notes

Reaction equation

HRID 1429318 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[Br:14][C:15]1[CH:27]=[CH:26][C:25]2[C:24]3[C:19](=[CH:20][C:21](I)=[CH:22][CH:23]=3)[C:18]([CH3:30])([CH3:29])[C:17]=2[CH:16]=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:14][C:15]1[CH:27]=[CH:26][C:25]2[C:24]3[C:19](=[CH:20][C:21]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)=[CH:22][CH:23]=3)[C:18]([CH3:30])([CH3:29])[C:17]=2[CH:16]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 453821792-Bromo-7-iodo-9,9-dimethyl-9H-fluorene

Product 1

HCID 576228742-bromo-9,9-dimethyl-7-(naphthalene-2-yl)-9H-fluoreneYield 76.1%

Reagents, catalysts & solvents 3

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

Procedure

In argon atmosphere, a mixture of 13.91 g (80.9 mmol) of 2-naphthaleneboronic acid, 30.0 g (80.9 mmol) of 2-bromo-7-iodo-9,9-dimethylfluorene, 4.67 g (4.0 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 200 ml of dimethoxyethane, and 122.36 g of a 2 M sodium carbonate aqueous solution was refluxed under stirring 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 residue was purified by silica gel chromatography to obtain 21.3 g (yield: 76.1%) of 2-bromo-9,9-dimethyl-7-(naphthalene-2-yl)-9H-fluorene.

Workup

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

Sources & evidence

ORD record
ord-28f40e28f10a42bb8e365ba43aea43bd
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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