ChemicalBook CAS DataBase List 6-Bromoindole-3-carboxaldehyde

6-Bromoindole-3-carboxaldehyde synthesis

10synthesis methods

Product Name:6-Bromoindole-3-carboxaldehyde
CAS Number:17826-04-9
Molecular formula:C9H6BrNO
Molecular Weight:224.05

52415-29-9
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50-00-0 Synthesis

50-00-0
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17826-04-9
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Yield:17826-04-9 73%

Reaction Conditions:

with iron(III) chloride;ammonia in water;N,N-dimethyl-formamide at 130; for 5 h;

Steps:

Indolecarbaldehydes 2a-2aa; General Procedure
General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37% aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25% aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 mol%), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane-EtOAc).

References:

Wang, Qing-Dong;Zhou, Bin;Yang, Jin-Ming;Fang, Dong;Ren, Jiangmeng;Zeng, Bu-Bing [Synlett,2017,vol. 28,# 19,p. 2670 - 2674] Location in patent:supporting information

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52415-29-9
412 suppliers
$9.00/1g