Sodium Carbonate → 3,5-Dipyrenylbromobenzene

HRID 228139Notes

Reaction equation

HRID 228139 reaction equation
Br[C:2]1[C:3](Br)=[C:4]([Br:8])[CH:5]=[CH:6][CH:7]=1.[C:10]1(B(O)O)[C:23]2[C:24]3=[C:25]4[C:20](=[CH:21][CH:22]=2)[CH:19]=[CH:18][CH:17]=[C:16]4[CH:15]=[CH:14][C:13]3=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:10]1([C:6]2[CH:5]=[C:4]([Br:8])[CH:3]=[C:2]([C:17]3[C:16]4[C:25]5=[C:24]6[C:13](=[CH:14][CH:15]=4)[CH:12]=[CH:11][CH:10]=[C:23]6[CH:22]=[CH:21][C:20]5=[CH:19][CH:18]=3)[CH:7]=2)[C:23]2[C:24]3=[C:25]4[C:20](=[CH:21][CH:22]=2)[CH:19]=[CH:18][CH:17]=[C:16]4[CH:15]=[CH:14][C:13]3=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 118421,2,3-TribromobenzeneHCID 5084102Pyren-1-ylboronic acid

Product 1

HCID 714247373,5-DipyrenylbromobenzeneYield 38.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under the atmosphere of argon gas, 6 g of tribromobenzene available as a commercial reagent, 9.4 g of 1-pyrenyl boronic acid and 0.88 g of tetrakis(triphenylphophine)palladium were dissolved in 150 ml of toluene, and then the 57 ml of 2M sodium carbonate aqueous solution was added therein, followed by 7 hours reflux on heating. After standing to cool, the precipitated solid was separated through filtration, and then followed by washing with water and methanol, and drying. The obtained solid was refined through a silica gel chromatography (developing solvent: toluene/hexane=1/3) and then 4.1 g of 3,5-dipyrenylbromobenzene of pale yellow solid was obtained (Yield: 38%).

Workup

  1. temperaturereflux
  2. temperatureon heating
  3. temperatureto cool
  4. customthe precipitated solid was separated through filtration
  5. washby washing with water and methanol
  6. customdrying

Sources & evidence

ORD record
ord-8ca79cd2f7be4a7193007483ffae5a51
Source dataset
uspto-grants-2009_07
Patent number
US07560604B2

Reaction notes

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