Potassium Hydroxide → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

HRID 1911572Notes

Reaction equation

HRID 1911572 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.[CH2:18]([CH:20]1[O:22][CH2:21]1)Br>CN(C=O)C>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:18][CH:20]3[CH2:21][O:22]3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 18430EpibromohydrinHCID 2748743,6-Dibromocarbazole

Product 1

HCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazoleYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following a literature procedure (Asso, V.; Ghilardi, E.; Bertini, S.; Digiacomo, M.; Granchi, C.; Minutolo, F.; Rapposelli, S.; Bortolato, A.; Moro, S. Macchia, M. Chem Med Chem, 2008, 3, 1530-1534) powdered KOH (0.103 g, 1.85 mmol) was added to a solution of 3,6-dibromocarbazole (0.500 g, 1.54 mmol) in DMF (1.5 mL) at ambient temperature and stirred for 30 min until dissolved. Epibromohydrin (0.32 mL, 3.8 mmol) was added via syringe and the reaction was stirred at room temperature overnight. Upon completion, the solution was partitioned between EtOAc and H2O. The aqueous layer was washed 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was recrystallized from EtOAc/Hexane to afford the desired product (389 mg, 66%).

Workup

  1. dissolutionuntil dissolved
  2. stirringthe reaction was stirred at room temperature overnight
  3. customUpon completion, the solution was partitioned between EtOAc and H2O
  4. washThe aqueous layer was washed 3× with EtOAc
  5. washthe combined organics were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-d95f6e491fcc4affa909ead20b279170
Source dataset
uspto-grants-2013_12
Patent number
US08604074B2

Reaction notes

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