Toluene → N-[4-Fluoro-2-[(2-methyl-2-propen-1-yl)oxy]phenyl]acetamide

Temperature

50 °C

3-Chloro-2-methylpropene (1.36 g, 15 mmol) was added to a mixture of 5-fluoro-2-nitro-phenol (1.57 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), tetrabutylammonium hydrogen sulfate (0.068 g, 0.2 mmol) and acetonitrile (30 ml), and the mixture was heated under reflux for 18 h. The cold reaction mixture was diluted with toluene and washed with 5% aqueous potassium carbonate, dried and evaporated. A part of the residue (0.631 g, 3 mmol), sodium dithionite (1.04 g, 6 mmol) in EtOH-THF-H2O (2:1:1, 3 ml) was heated at 75° C. for 4 h. The mixture was portioned between dichloromethane and 15% aqueous potassium carbonate and the organic solution dried and concentrated. The obtained residue was diluted with methanol (1.5 ml) and reacted with acetic anhydride (1.5 ml) at 50° C. for 2 min and allowed to attend room temperature during 20 min, then pyridine (4 ml) was added and the solution heated again at 50° C. for 3 min, cold and concentrated. The material was purified by silica gel chromatography (light petroleum-ethyl acetate 2:1) to give 95 mg of the subtitle compound.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 18 h
3. customThe cold reaction mixture
4. washwashed with 5% aqueous potassium carbonate
5. customdried
6. customevaporated
7. customthe organic solution dried
8. concentrationconcentrated
9. additionThe obtained residue was diluted with methanol (1.5 ml)
10. customreacted with acetic anhydride (1.5 ml) at 50° C. for 2 min
11. concentrationcold and concentrated
12. customThe material was purified by silica gel chromatography (light petroleum-ethyl acetate 2:1)

ORD record

ord-96ffccf4b04546b8aa5fea755347cdc6

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06927222B2