
5-Bromo-3-cyanoindole synthesis
- Product Name:5-Bromo-3-cyanoindole
- CAS Number:90271-86-6
- Molecular formula:C9H5BrN2
- Molecular Weight:221.05

10075-50-0

1189-71-5

90271-86-6
GENERAL METHOD: To a solution of 5-bromoindole (6.8 mmol) in anhydrous acetonitrile (6.0 mL) was slowly added chlorosulfonyl isocyanate (CSI) (0.63 mL, 7.25 mmol) dropwise at 0 °C, and the reaction mixture was kept stirring at 0 °C for 2 hours. Subsequently, anhydrous dimethylformamide (DMF) (1.3 mL, 170.0 mmol) was added dropwise and stirring was continued at 0 °C for 2 hours. Upon completion of the reaction, the mixture was poured into water and the resulting precipitate was collected by filtration. The precipitate was dried over anhydrous Na2SO4 and purified by column chromatography with the eluent being petroleum ether/ethyl acetate (40/60) or pure ethyl acetate to afford the target product 5-bromo-3-cyanoindole.

10075-50-0
697 suppliers
$5.00/10g

1189-71-5
362 suppliers
$18.00/5g

90271-86-6
107 suppliers
inquiry
Yield: 91%
Reaction Conditions:
Stage #1:5-bromo-1H-indole;isocyanate de chlorosulfonyle in acetonitrile at 0; for 2 h;
Stage #2: with N,N-dimethyl-formamide in acetonitrile at 0; for 2 h;
Steps:
3.1.2. General Procedure for the Synthesis of 1H-Indole-3-carbonitriles (4a-d)
General procedure: To a solution of the appropriate indoles 3a-d (6.8 mmol) in anhydrous acetonitrile (6.0 mL),chlorosulfonyl isocyanate (CSI) (0.63 mL, 7.25 mmol) was added dropwise at 0 °C and the reactionmixture was stirred at 0 °C for 2 h. Anhydrous dimethylformamide (DMF) (1.3 mL, 170.0 mmol)was added dropwise and the mixture was stirred at 0 C for 2 h. The mixture was poured intoice-water and the obtained precipitate was filtered off, dried (anhydrous Na2SO4) and purified bycolumn chromatography using petroleum ether/ethyl acetate (40/60) (for 4b-d) or ethyl acetate (for4a) as eluent.
References:
Carbone, Anna;Parrino, Barbara;Cusimano, Maria Grazia;Spanò, Virginia;Montalbano, Alessandra;Barraja, Paola;Schillaci, Domenico;Cirrincione, Girolamo;Diana, Patrizia;Cascioferro, Stella [Marine Drugs,2018,vol. 16,# 8,art. no. 274]

877-03-2
233 suppliers
$6.00/1g

90271-86-6
107 suppliers
inquiry

877-03-2
233 suppliers
$6.00/1g

90271-86-6
107 suppliers
inquiry

10075-50-0
697 suppliers
$5.00/10g

75-05-8
1038 suppliers
$10.00/10g

90271-86-6
107 suppliers
inquiry