3,6-Dibromocarbazole synthesis
- Product Name:3,6-Dibromocarbazole
- CAS Number:6825-20-3
- Molecular formula:C12H7Br2N
- Molecular Weight:325
Yield:1592-95-6 47%
Reaction Conditions:
with N-Bromosuccinimide in N,N-dimethyl-formamide at 0 - 20; for 24 h;
Steps:
3-Bromocarbazole (2):
2 was synthesised as reported previously[32,33]. A solution of N-bromosuccinimide (1.1 g,5.98 mmol) in dimethylformamide was added dropwise to asolution of carbazole (1, 1 g, 5.96 mmol) in dimethylformamide(15 mL) at 0 °C. The reaction mixture was then stirred atroom temperature for 24 h. The reaction was poured intodistilled water to give a cream coloured precipitate. The precipitatewas filtered off under vacuum and washed with distilledwater (3 × 20 mL). The precipitate was dissolved in ethylacetate, dried with sodium sulfate and filtered. Upon concentra tion under reduced pressure the crude product was obtained as abrown solid. After crystallisation of the crude product withchloroform, the pure product 2 (692 mg, 47%) was obtained aswhite crystals. Rf (ethyl acetate/hexane, 1:6 v/v): 0.43; meltingpoint: 200-201°C; 1H NMR (600 MHz, CDCI3) δ (ppm) 8.19(d, J = 1.9 Hz, 1H), 8.08 (s, 1H), 8.02 (dd, J = 7.7, 1.1 Hz, 1H),7.50 (dd, J = 8.5, 1.9 Hz, 1H), 7.47-7.40 (m, 2H), 7.31 (d, J =8.6 Hz, 1H), 7.25 (td, J = 6.3, 1.8 Hz, 1H).
References:
Altinolcek, Nuray;Battal, Ahmet;Peveler, William J.;Skabara, Peter J.;Tavasli, Mustafa;Yu, Holly A. [Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 1066 - 1074]
86-74-8
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