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ChemicalBook CAS DataBase List 4-BROMO-2,6-DIMETHOXYBENZENAMINE

4-BROMO-2,6-DIMETHOXYBENZENAMINE synthesis

3synthesis methods
-

Yield:23957-21-3 79%

Reaction Conditions:

with bromine in chloroform at 0 - 21; for 14 h;

Steps:

4-Bromo-2,6-dimethoxyaniline[14] (S4)

This reaction was not performed under inert conditions.A solution of bromine (1.00 mL, 3.12 g, 1.95 mmol, 1.00 equiv) in chloroform (50 mL) was added to asolution of 2,6-dimethoxyaniline (3.06 g, 2.00 mmol, 1.03 equiv) in chloroform (50 mL) at 0°C over thecourse of 1 h. Afterwards, the solution was warmed up to 21 °C and stirred for additional 14 h. Then,NaOH (2 M) was added to adjust the pH to 11. The water phase was extracted with ethyl acetate (3 ×100 mL). The combined organic phases were washed with water (100 mL), brine (100 mL), dried overMgSO4 and filtered. The crude product was purified by column chromatography (eluent: nhexane/DCM 95:5) to yield S4 as a colorless solid (3.66 g, 1.58 mmol, 79%, Lit.:[14] 77%)

References:

Schultzke, Sven;Staubitz, Anne;Walther, Melanie [Molecules,2021,vol. 26,# 13] Location in patent:supporting information