Acetic Anhydride → HCID 18423076, compound

To a solution of 4-bromomethyl-3-nitrobenzonitrile (25.7 g) in tetrahydrofuran (250 ml) was added a 2.0 M tetrahydrofuran solution (59 ml) of a borane-methylsulfide complex and the mixture was refluxed under heating for 4.5 hr. To the reaction mixture was added hydrochloric acid-methanol and the mixture was refluxed under heating for 1.5 hr. The solvent was evaporated under reduced pressure to give a brown oil. The obtained brown oil was crystallized from ethyl acetate to give yellow white crystals. To a mixed solution of the obtained yellow white crystals, acetic anhydride (12.1 ml), water (50 ml) and ethyl acetate (100 ml) was added an aqueous solution (50 ml) of sodium hydroxide (12.8 g) under ice-cooling. This reaction mixture was stirred at room temperature for 2.5 hr and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) to give the title compound (21.4 g) as a brown oil.

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 4.5 hr
3. temperaturethe mixture was refluxed
4. temperatureunder heating for 1.5 hr
5. customThe solvent was evaporated under reduced pressure
6. customto give a brown oil
7. customThe obtained brown oil was crystallized from ethyl acetate
8. customto give yellow white crystals
9. temperaturecooling
10. extractionextracted with ethyl acetate
11. washThe extract was washed with saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. customThe solvent was evaporated under reduced pressure
14. customThe obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1)

ORD record

ord-9d82420bafa04efdaa39263c03f4e603

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455528B1