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

HRID 1914415Notes

Reaction equation

HRID 1914415 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

Next, 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 gas stream and then 1.7 g of benzyltrimethylammonium tribromide dissolved in 5 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 2 hours and 20 ml of water was poured into the solution, followed by extraction with 20 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 10 ml of methanol was added, followed by standing overnight. The precipitated solid was filtered and then vacuum-dried to obtain 1.9 g of 1-bromo-7-t-butyl-3-phenylpyrene.

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with 20 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. additionTo the resulting solid, 10 ml of methanol was added
  7. waitby standing overnight
  8. filtrationThe precipitated solid was filtered
  9. customvacuum-dried

Sources & evidence

ORD record
ord-f7f2ce1f405844e584a7eb21cb4a4249
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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