ChemicalBook CAS DataBase List 3-Bromo-9H-carbazole

3-Bromo-9H-carbazole synthesis

12synthesis methods

Product Name:3-Bromo-9H-carbazole
CAS Number:1592-95-6
Molecular formula:C12H8BrN
Molecular Weight:246.1

3-Bromo-9H-carbazole synthesis: A solution of N-bromosuccinimide (1.1g, 5.98mmol) in dimethylformamide was added dropwise to a solution of carbazole (1, 1g, 5.96mmol) in dimethylformamide (15mL) at 0°C. The reaction mixture was then stirred at room temperature for 24h. The reaction was poured into distilled water to give a cream coloured precipitate. The precipitate was filtered off under vacuum and washed with distilled water (3 × 20mL). The precipitate was dissolved in ethyl acetate, dried with sodium sulfate and filtered. Upon concentration under reduced pressure the crude product was obtained as a brown solid. After crystallisation of the crude product with chloroform, the pure 3-Bromocarbazole(692 mg, 47%) was obtained as white crystals. Rf (ethyl acetate/hexane, 1:6 v/v): 0.43; melting point: 200–201°C.

21865-50-9 Synthesis

21865-50-9
62 suppliers
$9.00/250mg

1592-95-6
401 suppliers
$5.00/1g

Yield:1592-95-6 91%

Reaction Conditions:

with copper(II) choride dihydrate in dimethyl sulfoxide at 100; for 7 h;

Steps:

General procedure for the synthesis of compounds (2a-2q), (7a-7d), (9, 11, 13)
General procedure: A mixture of starting compound (2.69 mmol), CuCl₂.2H₂O (10 mol %) in DMSO (5 mL) stirred at 100 °C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles.

References:

Dalvi, Bhakti A.;Lokhande, Pradeep D. [Tetrahedron Letters,2018,vol. 59,# 22,p. 2145 - 2149] Location in patent:supporting information

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86-74-8 Synthesis