N-bromobutanimide → 3-Bromo-9-(naphthalen-1-yl)-9H-carbazole

HRID 579299Notes

Reaction equation

HRID 579299 reaction equation
[C:1]1([N:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:24]N1C(=O)CCC1=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:24][C:20]1[CH:21]=[CH:22][C:23]2[N:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 6262189-(1-Naphthyl)-9H-carbazole

Product 1

HCID 595611493-Bromo-9-(naphthalen-1-yl)-9H-carbazoleYield 99%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 200-mL conical flask, 5.9 g (20 mmol) of 9-(1-naphthyl)-9H-carbazole was dissolved in a mixture solvent of 50 mL of toluene and 70 mL of ethyl acetate, and then 3.6 g (20 mmol) of N-bromosuccinimide (abbreviation: NBS) was added to this solution. The mixture was stirred at room temperature for 36 hours. After completion of the reaction, this mixture solution was washed with water, and magnesium sulfate was added thereto so that moisture was adsorbed. This suspension was filtrated, and the obtained filtrate was concentrated and collected. As a result, 7.4 g of white powder that was an objective substance was obtained in a yield of 99%. The synthesis scheme of Step 1 is shown in (F6-1).

Workup

  1. customAfter completion of the reaction
  2. washthis mixture solution was washed with water, and magnesium sulfate
  3. additionwas added
  4. filtrationThis suspension was filtrated
  5. concentrationthe obtained filtrate was concentrated
  6. customcollected
  7. customwas obtained in a yield of 99%
  8. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-74b6fd5920a445918bc82d8e1a28fe1f
Source dataset
uspto-grants-2015_05
Patent number
US09040720B2

Reaction notes

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