Dimethylformamide → 1-(2-Naphthyl)pyrene

HRID 1027313Notes

Reaction equation

HRID 1027313 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.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:9]1[C:8]2[C:17]3=[C:16]4[C:5](=[CH:6][CH:7]=2)[CH:4]=[CH:3][CH:2]=[C:15]4[CH:14]=[CH:13][C:12]3=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 1596271-BromopyreneHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 540473501-(2-Naphthyl)pyreneYield 91.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixed solution of 7.0 g of 1-bromopyrene, 4.7 g of 2-naphthaleneboronic acid, 11.6 g of tripotassium phosphate, 1.8 g of tetrabutylammonium bromide, 0.11 g of palladium acetate and 248 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 5 hours. After cooling the solution to room temperature, 300 ml of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 100 ml of water. The resultant solid was dissolved in 200 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 100 ml of methanol, and then the precipitated solid was collected by filtration. The solid was vacuum-dried to obtain 7.5 g of 1-(2-naphthyl)pyrene.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. stirringby stirring at room temperature for 0.5 hours
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed twice with 100 ml of water
  5. dissolutionThe resultant solid was dissolved in 200 ml of dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. washthe residue was washed twice with 100 ml of methanol
  11. filtrationthe precipitated solid was collected by filtration
  12. customThe solid was vacuum-dried

Sources & evidence

ORD record
ord-74b2e57a6edd4d2396943891541c0bc1
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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