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 to 48% hydrobromic acid (8 ml) and the mixture was heated at 80-90° C. for 6 hours. The mixture was ice-cooled, and after dropwise addition of 4N-sodium hydroxide (32 ml), washed with toluene. 6N Hydrochloric acid was added to the aqueous layer to make pH 6.3. The mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (15 ml) and washed with water. Active charcoal (200 mg) was added, and the mixture was stirred at room temperature for 10 min. The mixture was filtrated and concentrated under reduced pressure. Ethyl acetate (10 ml) was added to the residue, and the mixture was refluxed. The mixture was allowed to cool and stirred for 30 min, and hexane (10 ml) was added. 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. washwashed 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. additionActive charcoal (200 mg) was added
7. filtrationThe mixture was filtrated
8. concentrationconcentrated under reduced pressure
9. additionEthyl acetate (10 ml) was added to the residue
10. temperaturethe mixture was refluxed
11. temperatureto cool
12. stirringstirred 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-ba153c31ed5a483b9faeec5ab5dffc42

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743924B2