ChemicalBook CAS DataBase List 2-AMINO-4-BROMOBENZALDEHYDE

2-AMINO-4-BROMOBENZALDEHYDE synthesis

8synthesis methods

Product Name:2-AMINO-4-BROMOBENZALDEHYDE
CAS Number:59278-65-8
Molecular formula:C7H6BrNO
Molecular Weight:200.03

5551-12-2

59278-65-8

Step 3. Synthesis of 2-amino-4-bromobenzaldehyde: Iron powder was added to 0.2 M of 4-bromo-2-nitrobenzaldehyde in a mixed solvent system of acetic acid and ethanol (v/v 1:1) under argon protection. The reaction mixture was stirred at room temperature for 1.5 h. The completion of the reaction was confirmed by LCMS monitoring. The insoluble solids were removed by filtration and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate, washed sequentially with saturated sodium bicarbonate solution and brine, and the organic phase was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by Biotage system using hexane solution of 15% ethyl acetate as eluent to afford the target compound 2-amino-4-bromobenzaldehyde in 38% yield.ES/MS m/z 200/202 (MH+).

5551-12-2 Synthesis

5551-12-2
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59278-65-8
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$45.00/500mg

Yield:59278-65-8 65%

Reaction Conditions:

with vasicine in ethylene glycol at 80; for 48 h;

Steps:

General procedure for reductive cyclization of o-nitrobenzaldehydes to 2,1-benzisoxazoles
General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.

References:

Sharma, Sushila;Kumar, Manoranjan;Bhatt, Vinod;Nayal, Onkar S.;Thakur, Maheshwar S.;Kumar, Neeraj;Singh, Bikram;Sharma, Upendra [Tetrahedron Letters,2016,vol. 57,# 45,p. 5003 - 5008] Location in patent:supporting information

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