Methanol → 1-Bromo-7-t-butyl-3-phenylpyrene

HRID 1670058Notes

Reaction equation

HRID 1670058 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:19]3=[C:20]4[C:10](=[CH:11][CH:12]=[C:13]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:14]4=[CH:15][CH:16]=[C:17]3[CH:18]=1)[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].CO.[Br-:29].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.O>ClCCl>[Br:29][C:11]1[C:10]2[C:20]3=[C:19]4[C:7](=[CH:8][CH:9]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:18]=[C:17]4[CH:16]=[CH:15][C:14]3=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 53442637BenzyltrimethylammoniumtribromideHCID 861012977-Tert-butyl-1-phenylpyrene

Product 1

HCID 861012991-Bromo-7-t-butyl-3-phenylpyreneYield 186.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixed solution of 1.5 g of 7-tert-butyl-1-phenylpyrene, 25 ml of dichloromethane and 8 ml of methanol was then cooled to 0° C. under a nitrogen stream, and a solution of 1.7 g of benzyltrimethylammonium tribromide in 5 ml of dichloromethane was added dropwise to the mixed solution. After the mixed solution was stirred at room temperature for 2 hours, 20 ml of water was added thereto, and the mixture was extracted with 20 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate, and then evaporated. Ten ml of methanol was added to the resulting solid and allowed to stand overnight. The precipitated solid was separated by filtration and dried under vacuum to give 1.9 g of 1-bromo-7-tert-butyl-3-phenylpyrene.

Workup

  1. extractionthe mixture was extracted with 20 ml of dichloromethane
  2. washThe organic layer was washed twice with 20 ml of water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionTen ml of methanol was added to the resulting solid
  6. waitto stand overnight
  7. customThe precipitated solid was separated by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2b30ff3445e34c2ab5ff191419f426df
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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