Methanol → HCID 86101303, compound

HRID 1914427Notes

Reaction equation

HRID 1914427 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][C:24]([CH3:27])=[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].ClCCl.CO.[Br-:33].[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>[Br-].[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>[Br:33][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])([CH3:3])[CH3:2])[CH:18]=[C:17]4[CH:16]=[CH:15][C:14]3=[C:13]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 53442637BenzyltrimethylammoniumtribromideHCID 86101302HCID 86101302, compound

Product 1

HCID 86101303HCID 86101303, compoundYield 168.6%

Reagents, catalysts & solvents 2

HCID 53442637BenzyltrimethylammoniumtribromideCatalystHCID 962WaterSolvent

Procedure

Next, a mixed solution of 7.63 g of 7-t-butyl-1-(4-methylphenyl)pyrene, 105 ml of dichloromethane and 35 ml of methanol was cooled to 0° C. under an argon gas stream and then 8.54 g of benzyltrimethylammonium tribromide was added over 5 minutes. This mixed solution was stirred at room temperature for 4 hours and 0.85 g of benzyltrimethylammonium tribromide was added, followed by stirring for 1.5 hours. To the reaction solution, 40 ml of water was poured, followed by extraction twice with 80 ml of dichloromethane. The combined organic layer was washed with 50 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 25 ml of methanol was added, and then the resulting solution was stirred for one hour, filtered and vacuum-dried to obtain 8.91 g of 1-bromo-7-t-butyl-3-(4-methylphenyl)pyrene.

Workup

  1. stirringby stirring for 1.5 hours
  2. extractionfollowed by extraction twice with 80 ml of dichloromethane
  3. washThe combined organic layer was washed with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. additionTo the resulting solid, 25 ml of methanol was added
  7. stirringthe resulting solution was stirred for one hour
  8. filtrationfiltered
  9. customvacuum-dried

Sources & evidence

ORD record
ord-717a3a4943d64b8e9e56c8dd66b0148f
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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