Benzyl Bromide → 4-Benzyl-3,5-dibromo-4H-1,2,4-triazole

Temperature

0 °C

To a solution of 3,5-dibromo-4H-1,2,4-triazole (3.0 g, 13.3 mmol) in DMF (10 mL) at 0° C. was added NaH (60% in mineral oil, 0.58 g, 14.5 mmol) (CAUTION: NaH and DMF can become a runaway reaction. All necessary safety precautions were performed). After the mixture was stirred at 0° C. for 30 minutes, benzyl bromide (1.57 mL, 13.2 mmol) was added. The mixture was stirred at 0° C. for 2 hours, then the mixture was partitioned between EtOAc (150 mL) and water (30 mL). The organic layer was washed with brine (2×30 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc 50:1 to 10:1) to yield 3.71 g (89%) of the title compound as a white solid. m/z (ES+) 316, 318, 320 (M+H)+.

1. customa runaway reaction
2. stirringThe mixture was stirred at 0° C. for 2 hours
3. customthe mixture was partitioned between EtOAc (150 mL) and water (30 mL)
4. washThe organic layer was washed with brine (2×30 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexanes:EtOAc 50:1 to 10:1)

ORD record

ord-b567d3bf526f44c4afdce7890ac4fe80

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2