Dimethylformamide → HCID 86101307, compound

HRID 1914420Notes

Reaction equation

HRID 1914420 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.[C:18]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].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:18]([C:22]1[CH:27]=[CH:26][C:25]([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:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 1596271-BromopyreneHCID 27343204-tert-Butylphenylboronic acid

Product 1

HCID 86101307HCID 86101307, compoundYield 79.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

A mixed solution of 2.0 g of 1-bromopyrene, 1.9 g of 4-t-butylphenylboronic acid, 3.1 g of tripotassium phosphate, 0.46 g of tetrabutylammonium bromide, 70 mg of palladium acetate and 70 mL of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 2 hours. The solution was cooled to room temperature and poured into 350 mL of water, and then the precipitated solid was collected by filtration. The resulting solid was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and then concentrated. The resulting crude product was purified by column chromatography and then vacuum-dried to obtain 1.9 g of 1-(4-t-butylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. dissolutionThe resulting solid was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by column chromatography
  8. customvacuum-dried

Sources & evidence

ORD record
ord-f371d2a4914848918c7f29e0ecba9426
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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