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ChemicalBook CAS DataBase List 2-Amino-5-bromo-4-methoxy-benzoic acid methyl ester

2-Amino-5-bromo-4-methoxy-benzoic acid methyl ester synthesis

3synthesis methods
50413-30-4 Synthesis
2-AMINO-4-METHOXY-BENZOIC ACID METHYL ESTER

50413-30-4
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2-Amino-5-bromo-4-methoxy-benzoic acid methyl ester

169044-96-6
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Yield: 82.06%

Reaction Conditions:

with bromine in dichloromethane at 20; for 20 h;

Steps:

Preparation of 2-amino-5-bromo-4-methoxybenzoate (35)
To a solution of compound 34 (4.0 g, 0.02 mol) in DCM(200 mL) was added bromine (1.36 mL, 0.02 mol). Themixture was stirred at room temperature for 20 h. It wasdiluted with saturated sodium hydrogen sulfite (50 mL) andthe aqueous solution was extracted with DCM. The combinedorganic layers were washed with brine, dried overNa2SO4 and filtered. The residue was purified by silica gelcolumn chromatography eluting with PE/EA to give whitepowder 35 (4.71 g, 82.06%). 35: 1H NMR δ (400 MHz,CDCl3) 8.04 (s, 1H), 6.14 (s, 1H), 5.87 (s, 2H), 3.89 (s, 3H),3.87 (s, 3H).

References:

Yi, Jingyu;Du, Guoxin;Zhao, Yuanyuan;Zhang, Liuqiang;Li, Bo;Zhu, Weiliang;Huang, Cheng;Li, Yiming;Guo, Fujiang [Medicinal Chemistry Research,2018,vol. 27,# 7,p. 1851 - 1862]