Water → 6-Bromo-1-fluoro-9-(2-nitrophenyl)-9H-carbazole

HRID 2277345Notes

Reaction equation

HRID 2277345 reaction equation
[F:1][C:2]1[C:14]2[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:31])C(=O)C1.O>C(Cl)Cl.C(#N)C>[Br:31][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])[C:14]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]2=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67324830fluoro-9-(2-nitrophenyl)-9H-carbazole

Product 1

HCID 673253476-Bromo-1-fluoro-9-(2-nitrophenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6.7 g (22.2 mmol) of fluoro-9-(2-nitrophenyl)-9H-carbazole are initially duced in 150 ml of CH2Cl2. A solution of 3.9 g (22.3 mmol) of NBS in 100 ml of acetonitrile is subsequently added dropwise at −15° C. with exclusion of light, and the mixture is stirred at room temperature for a further 4 h. For work-up, 150 ml of water are added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The product is washed by stirring with hot hexane and filtered off with suction.

Workup

  1. extractionis then extracted with CH2Cl2
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. washThe product is washed
  5. stirringby stirring with hot hexane
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-089e765732e54b7db601251d4cac6374
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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