Dimethylformamide → HCID 86101382, compound

HRID 1914401Notes

Reaction equation

HRID 1914401 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]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:25]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26].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>[C:25]([C:29]1[CH:34]=[CH:33][C:32]([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:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 27343204-tert-Butylphenylboronic acidHCID 58050554HCID 58050554, compound

Product 1

HCID 86101382HCID 86101382, compoundYield 66%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

A mixed solution of 4.0 g of 1-bromo-6-(4-chlorophenyl)pyrene, 2.0 g of 4-t-butylphenylboronic acid, 4.8 g of tripotassium phosphate, 0.72 g of tetrabutylammonium bromide, 52 mg of palladium acetate and 100 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 3 hours. The solution was cooled to room temperature and 100 ml of water was poured into the solution, followed by filtration. The resulting solid was dissolved at 140° C. by adding 100 ml of xylene. The solution was cooled to 100° C. and then filtered through Celite. The filtrate was evaporated, and then the resulting solid was washed with 50 ml of methanol and vacuum-dried to obtain 3.0 g of 1-(4-t-butylphenyl)-6-(4-chlorophenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. dissolutionThe resulting solid was dissolved at 140° C.
  4. additionby adding 100 ml of xylene
  5. temperatureThe solution was cooled to 100° C.
  6. filtrationfiltered through Celite
  7. customThe filtrate was evaporated
  8. washthe resulting solid was washed with 50 ml of methanol
  9. customvacuum-dried

Sources & evidence

ORD record
ord-a53323af69c74197940d4bad24eccaa4
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…