Dimethylformamide → HCID 86643022, compound

HRID 1027317Notes

Reaction equation

HRID 1027317 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.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.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>[F:19][C:20]1[CH:25]=[CH:24][C:23]([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:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 176470Pyrene, 1,6-Dibromo-HCID 2856454-Fluorophenylboronic acid

Product 1

HCID 86643022HCID 86643022, compoundYield 83%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

A mixed solution of 2 g of 1,6-dibromopyrene, 2.3 g of 4-fluorophenylboronic acid, 7.0 g of tripotassium phosphate, 1.1 g of tetrabutylammonium bromide, 74 mg of palladium acetate and 50 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 6 hours. After cooling the solution to room temperature, 50 ml of water was injected, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The resultant solid was washed with 30 ml of methanol and then vacuum-dried to obtain 1.8 g of 1,6-bis(4-fluorophenyl)pyrene.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. extractionfollowed by extraction with 100 ml of dichloromethane
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. washThe resultant solid was washed with 30 ml of methanol
  7. customvacuum-dried

Sources & evidence

ORD record
ord-cf100b9d76ae48c59e50bf89f51e44ea
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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