Sodium Carbonate → 1-Bromo-6-phenylpyrene

HRID 731505Notes

Reaction equation

HRID 731505 reaction equation
[Br:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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.C1(C)C=CC=CC=1>[C:19]1([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][C:2]([Br:1])=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 176470Pyrene, 1,6-Dibromo-

Product 1

HCID 578363331-Bromo-6-phenylpyreneYield 64.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Next, 18.0 g (50.0 mmol) of 1,6-dibromopyrene, 6.10 g (50.0 mmol) of phenylboronic acid, and 1.16 g (1.0 mmol, 2 mol %) of tetrakis(triphenylphosphine)palladium(0) were loaded into a 300-ml three-necked flask, and air in the container was replaced with argon. Further, 150 ml of toluene and 75 ml (3 eq) of a 2M aqueous solution of sodium carbonate were added to the mixture, and the whole was refluxed under heat in an oil bath at 100° C. for 8 hours. After one night, the precipitate was separated by filtration, and the filtrate (toluene solution) was purified by column chromatography, whereby 11.6 g of 1-phenyl-6-bromopyrene were obtained (64.6% yield).

Workup

  1. temperaturethe whole was refluxed
  2. waitAfter one night
  3. customthe precipitate was separated by filtration
  4. customthe filtrate (toluene solution) was purified by column chromatography

Sources & evidence

ORD record
ord-36b590feaf094f8c97a56ea5cffcf58a
Source dataset
uspto-grants-2009_09
Patent number
US07585574B2

Reaction notes

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