Ethyl Acetate → 3-Bromo-9-(naphthalen-1-yl)-9H-carbazole

HRID 926675Notes

Reaction equation

HRID 926675 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.C(OCC)(=O)C.[Br:30]N1C(=O)CCC1=O>C1(C)C=CC=CC=1>[Br:30][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 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 6262189-(1-Naphthyl)-9H-carbazole

Product 1

HCID 595611493-Bromo-9-(naphthalen-1-yl)-9H-carbazoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.9 g (20 mmol) of 9-(1-naphthyl)carbazole was put into a 500 mL Meyer flask, and 50 mL of ethyl acetate and 50 mL of toluene were added thereto, and the reaction mixture was stirred. Then, 3.6 g (20 mmol) of N-bromosuccinimide was slowly added to the solution, and the solution was stirred for about 170 hours (one week) at room temperature. After this solution was washed with water, the organic layer was dried with magnesium sulfate. Filtration and concentration of the reaction mixture gave 7.4 g of 3-bromo-9-(1-naphthyl)carbazole as white powder (99% yield). The Rf values (SiO2, eluent; hexane:ethyl acetate=2:1) of 3-bromo-9-(1-naphthyl)carbazole and 9-(1-naphthyl)carbazole were 0.43 and 0.35, respectively.

Workup

  1. additionwere added
  2. stirringthe solution was stirred for about 170 hours (one week) at room temperature
  3. washAfter this solution was washed with water
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. filtrationFiltration and concentration of the reaction mixture

Sources & evidence

ORD record
ord-b8d05e8e6629443bb1de758121a24e5a
Source dataset
uspto-grants-2016_03
Patent number
US09287511B2

Reaction notes

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