Methanol → HCID 15321723, compound

HRID 1914411Notes

Reaction equation

HRID 1914411 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]([CH3:21])[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-:24].[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:24][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]([CH3:21])[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 30866837-tert-Butyl-1-methylpyreneHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 15321723HCID 15321723, compoundYield 155.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Next, a mixed solution of 3 g of 7-t-butyl-1-methylpyrene, 130 ml of dichloromethane and 43 ml of methanol was cooled to 0° C. under a nitrogen gas stream and then 4.3 g of benzyltrimethylammonium tribromide dissolved in 5 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 4 hours and 50 ml of water was poured into the solution, followed by extraction with 50 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 3.4 g of 1-bromo-7-t-butyl-3-methylpyrene.

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with 50 ml of dichloromethane
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-de25a688f34444eb87a789c9a8ae07b5
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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