Hydrogen Bromide → 4-(4-[1,2,3]Triazol-1-yl-butyl)phenol

Temperature

85 °C

1-[4-(4-Methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate (4.0 g, 12.22 mmol) was added into 48% hydrobromic acid (8 ml) and the mixture was heated at 80-90° C. for 6 hours. The reaction mixture was ice-cooled and 4N-sodium hydroxide (32 ml) was added dropwise. The mixture was washed with toluene. 6N Hydrochloric acid was added to the aqueous layer to adjust pH to 6.3. The mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (15 ml) and then washed with water. Activated carbon (200 mg) was added and the mixture was stirred at room temperature for 10 min. The mixture was filtrated and concentrated under reduced pressure. To the residue was added ethyl acetate (10 ml), and the mixture was refluxed. After allowing to cool and stirring for 30 min, hexane (10 ml) was added and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 4-[4-(1H-1,2,3-triazol-1-yl)butyl]phenol (2.25 g, yield 85%).

1. temperaturecooled
2. washThe mixture was washed with toluene
3. addition6N Hydrochloric acid was added to the aqueous layer
4. extractionThe mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (15 ml)
5. washwashed with water
6. additionActivated carbon (200 mg) was added
7. filtrationThe mixture was filtrated
8. concentrationconcentrated under reduced pressure
9. additionTo the residue was added ethyl acetate (10 ml)
10. temperaturethe mixture was refluxed
11. temperatureto cool
12. stirringstirring for 30 min
13. additionhexane (10 ml) was added
14. stirringthe mixture was stirred at room temperature for 30 min
15. filtrationThe precipitated crystals were collected by filtration
16. customdried under reduced pressure

ORD record

ord-bf868528d95043828eef05bc7a0d9100

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743924B2