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ChemicalBook CAS DataBase List 5-BROMO-2-METHOXYANILINE
6358-77-6

5-BROMO-2-METHOXYANILINE synthesis

8synthesis methods
4-BROMO-2-NITROANISOLE

33696-00-3

5-BROMO-2-METHOXYANILINE

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).

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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

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