Pyrene, 1,6-Dibromo- → 1,6-Diisobutylpyrene

HRID 929276Notes

Reaction equation

HRID 929276 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.[CH2:19](B(O)O)[CH:20]([CH3:22])[CH3:21].O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:19]([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]([CH2:4][CH:5]([CH3:16])[CH3:6])=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1)[CH:20]([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 176470Pyrene, 1,6-Dibromo-HCID 2734395(2-Methylpropyl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 1237354951,6-DiisobutylpyreneYield 154.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1,6-dibromopyrene (15.13 g, 42.0 mmol), isobutyl boronic acid (27.58 g, 270 mmol), potassium phosphate tribasic monohydrate (53.94 g, 254 mmol), Pd2(dba)3 (3.02 g, 3.30 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.00 g, 2.45 mmol) in toluene (300 mL) was fully degassing by bubbling through with nitrogen. The reaction mixture was maintained at reflux under nitrogen for 16 h. The reaction mixture was cooled, then filtered through a pad of Celite and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using hexane to yield 1,6-diisobutylpyrene (10.18 g, 77% yield) as a white solid.

Workup

  1. customwas fully degassing
  2. customby bubbling through with nitrogen
  3. temperatureThe reaction mixture was maintained
  4. temperatureat reflux under nitrogen for 16 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered through a pad of Celite
  7. washwashed with toluene
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6823bbaf959641f78a55b0d5ccdda25b
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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