N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 658958Notes

Reaction equation

HRID 658958 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 about 12 hours at a room temperature. This glacial acetic acid solution was dropped in one litter of ice water while stirring them. A precipitated white solid was washed three times with water. This 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 recrystallized with methanol to obtain 28.4 g (the yield: 88%) of 3-bromo-9-phenylcarbazole, which was a white powder (Synthesis scheme (c-1)).

Workup

  1. stirringwhile stirring them
  2. washA precipitated white solid was washed three times with water
  3. dissolutionThis 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. customThe thus obtained residue was recrystallized with methanol

Sources & evidence

ORD record
ord-351b6cd7729d45d2a5ec89f094f9982c
Source dataset
uspto-grants-2011_12
Patent number
US08076676B2

Reaction notes

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