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

HRID 1404884Notes

Reaction equation

HRID 1404884 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

Then, a mixed solution of 1.5 g of 7-t-butyl-1-phenylpyrene, 25 ml of dichloromethane and 8 ml of methanol was cooled to 0° C. under a nitrogen stream, and 1.7 g of benzyltrimethylammonium tribromide dissolved in 5 ml of dichloromethane was added dropwise. After this mixed solution was stirred at room temperature for 2 hours, 20 ml of water was added, and this was extracted with 20 ml of dichloromethane. The organic layer was washed with 20 ml of water two times, dried with magnesium sulfate, and evaporated. To the resulting solid was added 10 ml of methanol, and this was allowed to stand overnight. The precipitated solid was filtered, and vacuum-dried to obtain 1.9 g of 1-bromo-7-t-butyl-3-phenylpyrene.

Workup

  1. additionwas added dropwise
  2. extractionthis was extracted with 20 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. additionTo the resulting solid was added 10 ml of methanol
  7. waitto stand overnight
  8. filtrationThe precipitated solid was filtered
  9. customvacuum-dried

Sources & evidence

ORD record
ord-8de4180fedd04ea5ae1038ce08cc96bf
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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