Dimethylformamide → HCID 86101302, compound

HRID 1914426Notes

Reaction equation

HRID 1914426 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=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:18]([C:10]1[CH:9]=[C:8]2[C:17]3=[C:16]4[C:5](=[CH:4][CH:3]=[C:2]([C:26]5[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=5)[C:15]4=[CH:14][CH:13]=[C:12]3[CH:11]=1)[CH:6]=[CH:7]2)([CH3:19])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 497657301-Bromo-7-(tert-butyl)pyrene

Product 1

HCID 86101302HCID 86101302, compoundYield 67.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

Next, a mixed solution of 11.0 g of 1-bromo-7-t-butylpyrene, 5.78 g of 4-methylphenylboronic acid, 18.05 g of tripotassium phosphate, 2.74 g of tetrabutylammonium bromide, 191 mg of palladium acetate and 220 ml of dimethylformamide was heated and stirred under an argon gas stream at 130° C. for 14 hours. The solution was cooled to room temperature and 250 ml of water was poured into the solution, followed by extraction with 250 ml of dichloromethane. The organic layer was washed three times with 250 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 7.63 g of 7-t-butyl-1-(4-methylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 250 ml of dichloromethane
  3. washThe organic layer was washed three times with 250 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-66e2dde0e5ee472592c23d17875badcb
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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