Dimethylformamide → 7-Tert-butyl-1-phenylpyrene

HRID 1404883Notes

Reaction equation

HRID 1404883 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

Then, a mixed solution of 2.3 g (content 79.2%) 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 at 130° C. for 2 hours under a nitrogen stream. After the mixture was cooled to room temperature, 30 ml of water was added, and this was extracted with 50 ml of dichloromethane. The organic layer was washed with 20 ml of water two times, dried with magnesium sulfate, and evaporated. This was purified by silica gel column chromatography, and vacuum-dried to obtain 1.5 g of 7-t-butyl-1-phenylpyrene.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthis was extracted with 50 ml of dichloromethane
  3. washThe organic layer was washed with 20 ml of water two times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customThis was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-ece24dec335c41aebb3eac9af21f1842
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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