N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 2408215Notes

Reaction equation

HRID 2408215 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>C(O)(=O)C>[Br:20][C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 708519-Phenylcarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Firstly, 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, and 17.8 g (100 mmol) of N-bromo succinic acid imide was slowly added thereto. The mixture was stirred for overnight at a room temperature. This glacial acetic acid solution was dropped in 1 L of ice water while stirring them. A precipitated white solid was washed three times with water. This white solid was dissolved in 150 ml of diethyl ether, and washed with a saturated sodium hydrogencarbonate solution and water. This organic layer was dried with magnesium sulfate, and filtered. The obtained filtrate was concentrated. The thus obtained residue was added with about 50 ml of methanol and uniformly dissolved therein by being irradiated with supersonic. This solution was left to precipitate a white solid. This solution was filtrated and the filtrate was dried to obtain 28.4 g (the yield: 88%) of 3-bromo-9-phenylcarbazole, which was a white powder.

Workup

  1. stirringwhile stirring them
  2. washA precipitated white solid was washed three times with water
  3. dissolutionThis white solid was dissolved in 150 ml of diethyl ether
  4. washwashed with a saturated sodium hydrogencarbonate solution and water
  5. dry with materialThis organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe obtained filtrate was concentrated
  8. additionThe thus obtained residue was added with about 50 ml of methanol
  9. dissolutionuniformly dissolved
  10. customby being irradiated with supersonic
  11. waitThis solution was left
  12. customto precipitate a white solid
  13. filtrationThis solution was filtrated
  14. customthe filtrate was dried

Sources & evidence

ORD record
ord-57fb2183993643beba54187d3890d59d
Source dataset
uspto-grants-2014_08
Patent number
US08815410B2

Reaction notes

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