Sodium Carbonate → HCID 23109684, compound

HRID 2100211Notes

Reaction equation

HRID 2100211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:18]1[C:31]2[C:32]3=[C:33]4[C:28](=[CH:29][CH:30]=2)[C:27](Br)=[CH:26][C:25](Br)=[C:24]4[CH:23]=[CH:22][C:21]3=[C:20](Br)[CH:19]=1>C1C=CC=CC=1.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:18]2[C:31]3[C:32]4=[C:33]5[C:28](=[CH:29][CH:30]=3)[C:27]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[CH:26][C:25]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[C:24]5[CH:23]=[CH:22][C:21]4=[C:20]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=3)[CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 671881,3,6,8-TetrabromopyreneHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 23109684HCID 23109684, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

4.4 equivalents of 3-chlorophenylboronic acid, 10 equivalents of sodium carbonate in a 2 mol/L aqueous solution, and 0.12 equivalents of tetrakis(triphenylphosphine)palladium (0) were added to one equivalent of 1,3,6,8-tetrabromopyrene obtained in the same way as for EXAMPLE 1, and the mixture was subjected to heating under refluxing to allow reaction for three hours, using benzene as a solvent. 1,3,6,8-tetra(3-chlorophenyl)pyrene was obtained after deposition and purification through recrystallization of the product.

Workup

  1. customobtained in the same way as for EXAMPLE 1
  2. temperatureto heating
  3. temperatureunder refluxing
  4. customreaction for three hours

Sources & evidence

ORD record
ord-85cf1e8248e94edc8e84ff6a7cf4336c
Source dataset
uspto-grants-2009_08
Patent number
US07571894B2

Reaction notes

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