Water → N-benzyl-3,6-dibromocarbazole

HRID 1784326Notes

Reaction equation

HRID 1784326 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1>[CH2:18]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 2802035N-benzyl-3,6-dibromocarbazoleYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 3,6-dibromocarbazole (9.75 g, 30 mmol) was slowly added to a suspension of sodium hydride (45 mmol) in dried THF (100 mL), and then stirred for 30 minutes at room temperature. Benzylbromide (6.72 g, 40 mmol) was dropped into the reaction mixture to be stirred for 20 hours. After addition of water (about 100 mL), a precipitated solid was filtrated, and the filtrate (residuum of the filtration) was washed with an aqueous sodium hydrogencarbonate solution, and then was dissolved in ethanol. The solution was dried by magnesium sulfate, filtrated and concentrated. The residuum was recrystallized with ethanol to give N-benzyl-3,6-dibromocarbazole as a white solid. The yield was 61%.

Workup

  1. stirringto be stirred for 20 hours
  2. filtrationa precipitated solid was filtrated
  3. filtrationthe filtrate (residuum of the filtration)
  4. washwas washed with an aqueous sodium hydrogencarbonate solution
  5. dissolutionwas dissolved in ethanol
  6. dry with materialThe solution was dried by magnesium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe residuum was recrystallized with ethanol

Sources & evidence

ORD record
ord-754682a7a8f443a6b5e6a05cf8a29108
Source dataset
uspto-grants-2009_03
Patent number
US07504162B2

Reaction notes

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