Sodium Carbonate → HCID 86084118, compound

HRID 2358509Notes

Reaction equation

HRID 2358509 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:21]1[C:34]2[C:35]3=[C:36]4[C:31](=[CH:32][CH:33]=2)[CH:30]=[CH:29][CH:28]=[C:27]4[CH:26]=[CH:25][C:24]3=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[C:1]1([C:11]2[CH:16]=[CH:15][C:14]([C:28]3[C:27]4[C:36]5=[C:35]6[C:24](=[CH:25][CH:26]=4)[CH:23]=[CH:22][CH:21]=[C:34]6[CH:33]=[CH:32][C:31]5=[CH:30][CH:29]=3)=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1596271-BromopyreneHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 86084118HCID 86084118, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

7.4 g of 4-(naphthalene-1-yl)phenyl boronic acid prepared by a well known method and 7.0 g of conventional 1-bromopyrene were dissolved in 80 ml of dimethoxyethane (DME). Subsequently, 0.58 g of tetrakistriphenylphosphine palladium and 40 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool and then an organic layer was extracted therefrom by toluene. The organic layer was washed by saturated salt water, followed by drying through anhydrous sodium sulfate, and then the organic solvent was removed by an evaporator. The residue was refined through a silica gel chromatography (a developing solvent: toluene) and then 10.0 g of 1-(4-naphthalene-1-yl-phenyl) pyrene was obtained. (yield: 99%)

Workup

  1. temperatureAfter heating
  2. temperaturerefluxing over 8 hours
  3. temperatureto cool
  4. extractionan organic layer was extracted
  5. washThe organic layer was washed by saturated salt water
  6. dry with materialby drying through anhydrous sodium sulfate
  7. customthe organic solvent was removed by an evaporator

Sources & evidence

ORD record
ord-a3547c00acfa4a82b7cf6e3ece6434b3
Source dataset
uspto-grants-2010_07
Patent number
US07763761B2

Reaction notes

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