N-bromobutanimide → HCID 21072273, compound

HRID 1432158Notes

Reaction equation

HRID 1432158 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([CH3:15])=[CH:9][CH:8]=3.[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([CH2:15][Br:23])=[CH:9][CH:8]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21072274HCID 21072274, compound

Product 1

HCID 21072273HCID 21072273, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 3-bromo-9-tert-butoxycarbonyl-6-methylcarbazole obtained from Example 25 (653 mg, 1.81 mmol) and recrystallised N-bromosuccinimide (355 mg, 2.00 mmol) in carbon tetrachloride was refluxed under nitrogen with irradiation from a 150W halogen lamp for 2.5 h. The reaction mixture was cooled over an ice bath and filtered, and the filtrate evaporated. The crude product was chromatographed (PS with gradient elution to PS:DCM 1:1) to afford 3-bromo-6-bromomethyl-9-tert-butoxycarbonylcarbazole (551 mg, 1.26 mmol, 69%) as a colourless solid, mp 150° C. (dec).

Workup

  1. temperatureThe reaction mixture was cooled over an ice bath
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customThe crude product was chromatographed
  5. wash(PS with gradient elution to PS:DCM 1:1)

Sources & evidence

ORD record
ord-338682fefcc24a20b4c39d28ab97b976
Source dataset
uspto-grants-2009_11
Patent number
US07612036B2

Reaction notes

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