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

HRID 1485586Notes

Reaction equation

HRID 1485586 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 introduced 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 allowed to come to room temperature and is stirred at this temperature for a further 4 h. 150 ml of water are subsequently added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvents are removed in vacuo. The product is washed by stirring with hot hexane, and the solid is isolated.

Workup

  1. customto come to room temperature
  2. extractionis then extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvents are removed in vacuo
  5. washThe product is washed
  6. stirringby stirring with hot hexane
  7. customthe solid is isolated

Sources & evidence

ORD record
ord-d01b95dd9dd44c08972351726144fff7
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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