ChemicalBook CAS DataBase List 5-BROMO-2-METHOXYANILINE

5-BROMO-2-METHOXYANILINE synthesis

8synthesis methods

Product Name:5-BROMO-2-METHOXYANILINE
CAS Number:6358-77-6
Molecular formula:C7H8BrNO
Molecular Weight:202.05

33696-00-3

6358-77-6

General procedure for the synthesis of 5-bromo-2-methoxyaniline from 2-nitro-4-bromoanisole: 1. Preparation of Intermediate 11A: An ethanol (65 mL) solution of 4-bromo-1-methoxy-2-nitrobenzene (2.00 g, 8.62 mmol), zinc powder (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) was stirred for 2 hours at room temperature. 2. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and filtered through diatomaceous earth (CELITE). 3. The filtrate was concentrated by evaporation to give Intermediate 11A (1.74 g, 100% yield) as an off-white solid. 4. Mass spectral analysis (LCMS-ESI) of Intermediate 11A showed m/z 202,204 ([M+H]? , [M+2+H]?) , and a retention time (RT) of 0.70 min (Method J).

33696-00-3
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$10.00/1g

6358-77-6
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$6.00/250mg

Yield: 100%

Reaction Conditions:

with ammonium chloride;zinc in ethanol at 20; for 2 h;

Steps:

[00169] Intermediate 1 1 A. 4-Bromo-l-methoxy-2-nitrobenzene
[00169] Intermediate 1 1 A. 4-Bromo-l-methoxy-2-nitrobenzene: The mixture of 4- bromo- 1 -methoxy-2 -nitrobenzene (2.00 g, 8.62 mmol), zinc (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) in ethanol (65 mL) was stirred together at room temperature for 2 h. The reaction was then diluted with EtOAc, filtered through CELITE, and evaporated to give Intermediate 11A (1.74 g, 100%) as a grayish-white solid. LCMS (ESI) m/z 202, 204 (M+H, M+2+H)+, RT = 0.70 min (Method J).

References:

BRISTOL-MYERS SQUIBB COMPANY;L'HEUREUX, Alexandre;HIEBERT, Sheldon;HU, Carol;LAM, Patrick Y.S.;LLOYD, John;PI, Zulan;QIAO, Jennifer X.;THIBEAULT, Carl;TORA, George O.;YANG, Wu;WANG, Yufeng;WANG, Tammy C.;BOWSHER, Michael S.;RUEL, Rejean WO2014/22343, 2014, A1 Location in patent:Paragraph 00169

104-92-7 Synthesis