Dimethylformamide → 7-Tert-butyl-1-phenylpyrene

HRID 1670057Notes

Reaction equation

HRID 1670057 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

A mixed solution of 2.3 g of 1-bromo-7-tert-butylpyrene, 1.1 g of phenylboronic acid, 3.8 g of tribasic potassium phosphate, 0.58 g of tetrabutylammonium bromide, 12 mg of palladium acetate, and 30 ml of dimethylformamide was then 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 thereto, and the mixture was extracted with 50 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate, and then evaporated. The resulting residue was purified by silica gel column chromatography and dried under vacuum to give 1.5 g of 7-tert-butyl-1-phenylpyrene.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe mixture was extracted 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 resulting residue was purified by silica gel column chromatography
  7. customdried under vacuum

Sources & evidence

ORD record
ord-953b3e3a77a74868b757fd9d5c276e25
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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