ChemicalBook CAS DataBase List 3-bromo-2-chloroaniline

3-bromo-2-chloroaniline synthesis

6synthesis methods

Product Name:3-bromo-2-chloroaniline
CAS Number:56131-46-5
Molecular formula:C6H5BrClN
Molecular Weight:206.47

3970-37-4

56131-46-5

General procedure for the synthesis of 3-bromo-2-chloroaniline from 1-bromo-2-chloro-3-nitrobenzene: A mixed solution of 1-bromo-2-chloro-3-nitrobenzene (2.7 g, 11.44 mmol) and SnCl2 (12.97 g, 57.20 mmol) in ethanol (60 mL) was stirred and reacted for 3 hr under reflux conditions. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with deionized water followed by extraction with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent ratio of ethyl acetate/petroleum ether=1:50 to afford the target product 3-bromo-2-chloroaniline as an off-white solid (1.3 g, 55.2% yield).

3970-37-4 Synthesis

3970-37-4
134 suppliers
$11.00/250mg

56131-46-5
81 suppliers
$6.00/100mg

Yield:56131-46-5 100%

Reaction Conditions:

with iron;acetic acid in ethanol;water at 20; for 16 h;

Steps:

5 3-Bromo-2-chlorobenzenamine
To a mixture of l-bromo-2-chloro-3 -nitrobenzene (15.0 g, 63.60 mmol), HOAc (20 mL), EtOH (120 mL) and H₂0 (40 mL) at RT, iron powder (10.7 g, 190.70 mmol) was added in portions. The resulting mixture was stirred at RT for 16 h and then was neutralized with NaOH (5 N) solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na₂S0₄ and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate = 10: 1) to afford the desired product (14.0 g, 100% yield).

References:

ARAXES PHARMA LLC;LI, Liansheng;FENG, Jun;LONG, Yun, Oliver;LIU, Yuan;WU, Tao;REN, Pingda;LIU, Yi WO2017/15562, 2017, A1 Location in patent:Page/Page column 101

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58534-94-4 Synthesis