Sodium Carbonate → 9,9-Dioctyl-2-(4-nonylphenyl)-7-octyloxyfluorene

HRID 1243258Notes

Reaction equation

HRID 1243258 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](OCCCCCCCC)=[CH:9][CH:10]=3)[C:5]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:4]=2[CH:3]=1.[CH2:40]([C:49]1[CH:54]=[CH:53][C:52](B(O)O)=[CH:51][CH:50]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].[C:58](=[O:61])([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.CN(C)C=O>[CH2:32]([C:5]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:4]2[CH:3]=[C:2]([C:52]3[CH:53]=[CH:54][C:49]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[CH:50][CH:51]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([O:61][CH2:58][CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH3:11])=[CH:9][CH:10]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4589192B-(4-Nonylphenyl)boronic acidHCID 219245022-Bromo-9,9-dioctyl-7-octyloxyfluorene

Product 1

HCID 219245159,9-Dioctyl-2-(4-nonylphenyl)-7-octyloxyfluorene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of tetrakis(triphenylphosphine)palladium(0) (0.5 g, 4.64×10−4 mol), 2-bromo-9,9-dioctyl-7-octyloxyfluorene (5.04 g, 0.00844 mol), 4-nonylphenylboronic acid (2.30 g, 0.00929 mol), 20% aqueous sodium carbonate solution (40 cm3) and N,N-dimethylformamide (150 cm3) was heated under reflux overnight. The reaction mixture was filtered and extracted into diethyl ether (2×100 cm3). The combined organic layers were washed with water (2×100 cm3), dried (MgSO4), filtered and the solvent removed under partially reduced pressure. The residue was purified by column chromatography [silica gel, dichloromethane: hexane: 30:70] (yield 3.65 g, 60.0%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. extractionextracted into diethyl ether (2×100 cm3)
  5. washThe combined organic layers were washed with water (2×100 cm3)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under partially reduced pressure
  9. customThe residue was purified by column chromatography [silica gel, dichloromethane: hexane: 30:70] (yield 3.65 g, 60.0%)

Sources & evidence

ORD record
ord-ada872315dcf45da9398973942dc6f75
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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