Hydrochloric Acid → 4-Bromo-5-methoxy-2-methylaniline

Temperature

95 °C

N-(4-bromo-5-methoxy-2-methylphenyl)acetamide was dissolved in methanol (15 mL) and concentrated HCl (30 mL). The mixture was refluxed at 95° C. overnight. After cooling to room temperature, the mixture was poured into ice water, and basified to pH=12 with conc. NaOH aqueous solution. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated. The crude product was purified by silica chromatography (15% ethyl acetate in hexanes) to give 4-bromo-5-methoxy-2-methylaniline as a beige solid; 1H NMR (400 mHz, CDCl3) 7.20 (s, 1H), 6.37 (s, 1H), 4.6 (br, 2H), 3.82 (s, 3H), 2.12 (s, 3H).

1. temperatureAfter cooling to room temperature
2. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
3. dry with materialThe combined organic layer was dried over Na2SO4
4. concentrationconcentrated
5. customThe crude product was purified by silica chromatography (15% ethyl acetate in hexanes)

ORD record

ord-997572087dea4e39bea1f5fe0636959a

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859574B2