Dimethylformamide → HCID 86101313, compound

HRID 1914422Notes

Reaction equation

HRID 1914422 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.[CH3:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[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>[CH3:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[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:2]3[C:15]6[C:16](=[CH:17][CH:12]=[CH:13][CH:14]=6)[C:5]([CH3:6])=[CH:4][CH:3]=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 27735114-Methyl-1-naphthaleneboronic acid

Product 1

HCID 86101313HCID 86101313, compoundYield 126.8%

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 g of 4-methyl-1-naphthaleneboronic acid, 2.9 g of tripotassium phosphate, 0.59 g of tetrabutylammonium bromide, 40 mg of palladium acetate and 100 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 9 hours. The solution was cooled to room temperature and 500 ml of water was poured into the solution, followed by extraction with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then concentrated by evaporation. The resulting concentrate was recrystallized from toluene and then vacuum-dried at 70° C. to obtain 1.7 g of 1,6-di(4-methylnaphthalen-1-yl)pyrene as an opaque white powder.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 200 ml of dichloromethane
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. concentrationThe resulting concentrate
  7. customwas recrystallized from toluene
  8. customvacuum-dried at 70° C.

Sources & evidence

ORD record
ord-633e0b737d0b4e66bfaaca14e2edbe8c
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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