Dimethyl sulfite → 5-Bromo-2-chloro-4-methoxybenzonitrile

Temperature

75 °C

To a solution 5-bromo-2-chloro-4-hydroxybenzonitrile (2, 29 g, 124 mmol) in tetrahydrofuran (500 mL) was added lithium hydroxide monohydrate (6.7 g, 161 mmol) and dimethyl sulfite (15.2 mL, 161 mmol). The resulting mixture was heated at 75° C. for 5 h, re-cooled to room temperature, and quenched with water. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes) to yield the title compound (26 g, 104 mmol, 85%) as a white solid.

1. temperaturere-cooled to room temperature
2. customquenched with water
3. extractionThe mixture was extracted with ethyl acetate
4. washthe organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

ORD record

ord-f215bb61d46245049317e9eec02a036c

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921412B2