Dimethylformamide → HCID 58050547, compound

HRID 1914397Notes

Reaction equation

HRID 1914397 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][CH:2]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 1596271-Bromopyrene

Product 1

HCID 58050547HCID 58050547, compoundYield 88.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

A mixed solution of 59 g of 1-bromopyrene, 40 g of p-chlorophenylboronic acid, 108 g of tripotassium phosphate, g of tetrabutylammonium bromide, 1.15 g of palladium acetate and 1,250 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 1,000 ml of water was poured into the solution, followed by filtration. The resulting solid was washed with 200 ml of methanol, dissolved in 1,000 ml of dichloromethane, dried over magnesium sulfate, filtered through Celite and then evaporated. The resulting solid was washed with 200 ml of methanol and then vacuum-dried to obtain 58.2 g of 1-(4-chlorophenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. washThe resulting solid was washed with 200 ml of methanol
  4. dissolutiondissolved in 1,000 ml of dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through Celite
  7. customevaporated
  8. washThe resulting solid was washed with 200 ml of methanol
  9. customvacuum-dried

Sources & evidence

ORD record
ord-093e8cb2bfc4438d8da0f9b1b96ea64f
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…