Toluene → 1,6-Diphenylpyrene

HRID 1012907Notes

Reaction equation

HRID 1012907 reaction equation
Br[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+].[C:34]1(C)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O>[C:19]1([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 176470Pyrene, 1,6-Dibromo-

Product 1

HCID 591334031,6-DiphenylpyreneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

In a stream of argon, 20 g (55.6 mmol) of 1,6-dibromopyrene, 16.3 g (133 mmol) of phenyl boronic acid, 2.5 g (4 mol %) of tetrakistriphenylphosphine palladium, an aqueous solution containing 26.5 g (65 mmol) of sodium carbonate in 125 mL of water, and 250 mL of toluene were added to a 1-L three-necked flask equipped with a cooling pipe, and the whole was refluxed under heat at 100° C. for 8 hours. After the completion of the reaction, 50 mL of water was added and then a crystal was filtered out, washed with 50 mL of water, 100 mL of ethanol, and 100 mL of toluene. As a result, 15.3 g of 1,6-diphenylpyrene (a white powder) was obtained (99% yield).

Workup

  1. additionwere added to a 1-L three-necked flask
  2. customequipped with a cooling pipe
  3. temperaturethe whole was refluxed
  4. additionwas added
  5. filtrationa crystal was filtered out
  6. washwashed with 50 mL of water, 100 mL of ethanol, and 100 mL of toluene

Sources & evidence

ORD record
ord-d37b9a12e8084b1fbfd2a2000a4239d7
Source dataset
uspto-grants-2011_07
Patent number
US07981523B2

Reaction notes

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