Toluene → 1,6-Diphenylpyrene

HRID 530183Notes

Reaction equation

HRID 530183 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>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.O1CCCC1>[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

7

Reactant 4

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

Product 1

HCID 591334031,6-Diphenylpyrene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 15.0 g of 1,6-dibromopyrene, 13.2 g of phenylboronic acid, 1.9 g of tetrakis(triphenylphosphine)palladium (0) [Pd(PPh3)4], 27.8 g of sodium carbonate (130 mL of clean water), toluene and tetrahydrofuran were placed into a flask, and the resulting mixture was allowed to react at 90° C. for 7 hours. After cooling, the reaction solution was filtered, and solids obtained were washed with methanol and clean water. Further, the solids were purified by silica gel chromatography (heated toluene). The resulting crude product which was obtained by a concentration was re-crystallized from toluene, followed by drying under a reduced pressure, whereby white solids of 1,6-diphenylpyrene (11.8 g) were obtained.

Workup

  1. customto react at 90° C. for 7 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction solution was filtered
  4. customsolids obtained
  5. washwere washed with methanol and clean water
  6. customFurther, the solids were purified by silica gel chromatography (heated toluene)

Sources & evidence

ORD record
ord-67f7b26c2ed24c3ebedb3ecc71d7e8b7
Source dataset
uspto-grants-2016_05
Patent number
US09353027B2

Reaction notes

Loading…