Hydrochloric Acid → 2-Chloro-4-methoxyaniline

A mixture of 4-bromo-2-chloro-aniline (25.0 g, 121 mmol), copper iodide (23.1 g, 121 mmol), and a solution of sodium methoxide in methanol (28%, 125 mL) was stirred for 1 h at 100° C. The reaction mixture was poured into a mixture of hydrochloric acid (6 M, 100 mL) and ice, and washed with ethyl acetate. The aqueous phase was basified with aqueous sodium hydroxide (8 M) and extracted with ethyl acetate. The extracts was washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane gradient mixture to give the title compound as a pale yellow oil (7.90 g, 50.1 mmol, 41%).

1. washwashed with ethyl acetate
2. extractionextracted with ethyl acetate
3. washThe extracts was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltrated
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane gradient mixture

ORD record

ord-5162ac3db5174f008e476b2fe794d135

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785460B2