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

HRID 1970768Notes

Reaction equation

HRID 1970768 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-021c4300757247868908caee5e0fce0f
Source dataset
uspto-grants-2013_04
Patent number
US08431252B2

Reaction notes

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