Cesium carbonate → 1-Phenylpyrene

HRID 1670059Notes

Reaction equation

HRID 1670059 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][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCOCC1>[C:18]1([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][CH:2]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 1596271-Bromopyrene

Product 1

HCID 6242141-PhenylpyreneYield 83.8%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 44558591Tri-t-butylphosphine fluoroborateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixed solution of 9.4 g of 1-bromopyrene, 4.5 g of phenylboronic acid, 13 g of cesium carbonate, 348 mg of (tri-tert-butylphosphine) tetrafluoroborate, 575 mg of bis(dibenzylideneacetone)palladium(0), and 33 ml of 1,4-dioxane was heated and stirred at 100° C. for 3 hours under a nitrogen stream. The solution was cooled to room temperature and then filtered through celite. The filtrate was evaporated, and the resulting concentrate was purified by silica gel column chromatography and dried under vacuum to give 7.8 g of 1-phenylpyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through celite
  3. customThe filtrate was evaporated
  4. concentrationthe resulting concentrate
  5. customwas purified by silica gel column chromatography
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5bb85e5a7b18448e88f8b701d96b321c
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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