1,3-Dibromopropane → 3,6-dibromo-9-(3-bromopropyl)-9H-carbazole

HRID 922150Notes

Reaction equation

HRID 922150 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.[Br:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C.CCOC(C)=O>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:21][CH2:20][CH2:19][Br:18])[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 580972043,6-dibromo-9-(3-bromopropyl)-9H-carbazoleYield 28.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Crushed KOH (0.0673 g, 1.20 mmol, 1.2 equiv) was added to 3,6-dibromocarbazole (0.3250 g, 1.00 mmol) in 2 mL DMF solution and the mixture was stirred for 30 min. 1,3-dibromopropane (0.5047 g, 2.50 mmol, 2.5 equiv) in 3 mL DMF solution was added dropwise into the mixture and it was stirred at room temperature overnight. The crude reaction mixture was diluted with 30 mL EtOAc and washed with 1M HCl 2×10 mL and water 3×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.1275 g colorless oil as product, yield 28.6%.

Workup

  1. stirringwas stirred at room temperature overnight
  2. customThe crude reaction mixture
  3. washwashed with 1M HCl 2×10 mL and water 3×10 mL
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customevaporated
  6. customto afford the crude product, which

Sources & evidence

ORD record
ord-3c3a739fc9204d3799ca2de628582178
Source dataset
uspto-grants-2016_03
Patent number
US09278923B2

Reaction notes

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