Dimethylformamide → HCID 86101369, compound

HRID 1914398Notes

Reaction equation

HRID 1914398 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]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:26](B(O)O)=[CH:27][CH:28]=[CH:29][CH:30]=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>[C:25]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=1[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:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 4589187Biphenyl-2-boronic acidHCID 58050554HCID 58050554, compound

Product 1

HCID 86101369HCID 86101369, compoundYield 61.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

Next, a mixed solution of 4.9 g of 1-bromo-6-(4-chlorophenyl)pyrene, 3.7 g of 2-biphenylboronic acid, 8.0 g of tripotassium phosphate, 1.2 g of tetrabutylammonium bromide, 84 mg of palladium acetate and 125 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 6 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 washed with 50 ml of methanol, dissolved in 100 ml of dichloromethane, dried over magnesium sulfate, filtered and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 3.6 g of 1-(biphenyl-2-yl)-6-(4-chlorophenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. washThe resulting solid was washed with 50 ml of methanol
  4. dissolutiondissolved in 100 ml of dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe concentrate was purified by silica gel column chromatography
  9. customvacuum-dried

Sources & evidence

ORD record
ord-72c7e771625048b7bed44b2653fdc7bb
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…