Methyl iodide → 5-Bromo-2-chloro-4-methoxybenzonitrile

To a solution of 5-bromo-2-chloro-4-hydroxybenzonitrile (7.0 g, 30.11 mmol) in DMF (70 mL) was added cesium carbonate (19.62 g, 60.22 mmol, GLR Scientific) and MeI (3.74 mL, 60.22 mmol, Spectrochem). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with ice cold water (500 mL) and extracted with ethyl acetate (2×500 mL). The combined organic layer was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography (silica gel 100-200 mesh and 0-4% EtOAc in hexane) to obtain 5-bromo-2-chloro-4-methoxybenzonitrile (5.5 g, 74.1%) as white solid. m/z (ESI) N/A (no ionization observed).

1. customThe reaction mixture was quenched with ice cold water (500 mL)
2. extractionextracted with ethyl acetate (2×500 mL)
3. washThe combined organic layer was washed with water
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto obtain the crude compound which
8. customwas purified by column chromatography (silica gel 100-200 mesh and 0-4% EtOAc in hexane)

ORD record

ord-7f0ccf5aaedf4917873b7b602bc67ad6

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012443B2