Dimethylformamide → 7-Tert-butyl-1-phenylpyrene

HRID 1914414Notes

Reaction equation

HRID 1914414 reaction equation
BrC1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10](C(C)(C)C)[CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=CC=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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:8]([C:10]1[CH:9]=[C:8]2[C:17]3=[C:16]4[C:5](=[CH:6][CH:5]=[C:16]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:15]4=[CH:14][CH:13]=[C:12]3[CH:11]=1)[CH:6]=[CH:7]2)([CH3:17])([CH3:9])[CH3:7]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 497657301-Bromo-7-(tert-butyl)pyrene

Product 1

HCID 861012977-Tert-butyl-1-phenylpyreneYield 131.5%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

Next, a mixed solution of 2.3 g of 1-bromo-7-t-butylpyrene, 1.1 g of phenylboronic acid, 3.8 g of tripotassium phosphate, 0.58 g of tetrabutylammonium bromide, 12 mg of palladium acetate and 30 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 30 ml of water was poured into the solution, followed by extraction with 50 ml of dichloromethane. The organic layer was washed twice with 20 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 1.5 g of 7-t-butyl-1-phenylpyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 50 ml of dichloromethane
  3. washThe organic layer was washed twice with 20 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-4c61b31a1f84426f86ba18c849d2bf80
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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