N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1516995Notes

Reaction equation

HRID 1516995 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]1([N:15]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[Br:8][C:24]1[CH:25]=[CH:26][C:27]2[N:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 708519-Phenylcarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (19.31 g, 109 mmol) in DMF was added to 9-phenyl-9H-carbazole (24 g, 99 mmol) in 200 mL at 0° C. dropwise. The reaction was monitored by HPLC. The reaction was quenched by adding 500 mL of water after 2 h. After stirring at room temperature for 24 h, the clear solution was decanted and solid residue was dissolved in dichloromethane and washed with water and LiCl solution. The solution was dried with MgSO4 and the solvent was evaporated. The residue was used for the next step without further purification. The product contains starting material, monobromo, and dibromo. 31 g of product was obtained.

Workup

  1. customThe reaction was quenched
  2. additionby adding 500 mL of water after 2 h
  3. customthe clear solution was decanted
  4. dissolutionsolid residue was dissolved in dichloromethane
  5. washwashed with water and LiCl solution
  6. dry with materialThe solution was dried with MgSO4
  7. customthe solvent was evaporated
  8. customThe residue was used for the next step without further purification

Sources & evidence

ORD record
ord-c9209c04d95442b4a4bd105f0622445e
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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