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ChemicalBook CAS DataBase List 4-BROMO-3-ETHOXYANILINE HYDROCHLORIDE
125756-95-8

4-BROMO-3-ETHOXYANILINE HYDROCHLORIDE synthesis

3synthesis methods
423165-33-7 Synthesis
2-BROMO-5-NITROETHOXYBENZENE

423165-33-7
84 suppliers
$5.00/250mg

-

Yield: 86%

Reaction Conditions:

with iron;ammonium chloride in methanol;water at 80; for 3 h;

Steps:

Intermediate 8:
To a mixture of iron (0.851 g, 15.2 mmol) and ammonium chloride (0.815 g, 15.2 mmol) in water (30 mL), was added a solution of Intermediate 8A (0.61 g, 2.62 mmol, 86% yield) in methanol (15 mL). The reaction mixture was stirred at 80 °C for 3 h. Thereaction mixture was cooled to rt, filtered through CELITE, and the filtrate wasconcentrated. The residue obtained was dissolved in EtOAc (75 mL), washed with waterand brine, dried over Na2SO4 and concentrated to give Intermediate 8 (0.61 g, 2.62 mmol,86% yield). MS(ESI) m/z: 217.0 (M+H) ‘H NMR (300 MHz, DMSO-d6) ? ppm 7.09 (d,J = 8.5 Hz, 1 H), 6.29 (d, J = 2.4 Hz, 1 H), 6.09 (dd, J = 2.4, 8.5 Hz, 1 H), 5.25 (s, 2 H),3.96 (q, J = 7.0 Hz, 2 H), 1.32 (t, J = 7.0 Hz, 3 H).

References:

BRISTOL-MYERS SQUIBB COMPANY;GLUNZ, Peter W.;SITKOFF, Doree F.;BODAS, Mandar Shrikrishna;YADAV, Navnath Dnyanoba;PATIL, Sharanabasappa;RAO, Prasanna Savanor Maddu;THIYAGARAJAN, Kamalraj;MAISHAL, Tarun Kumar WO2016/144936, 2016, A1 Location in patent:Page/Page column 111; 112

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