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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence