Tetrabutylammonium Fluoride → 1-(2-Bromo-5-fluorophenyl)-1H-1,2,3-triazole

Temperature

25 °C

1-(2-Bromo-5-fluorophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole (0.800 g, 2.55 mmol) was dissolved in THF (10 mL) and tetrabutylammonium fluoride (2.8 mL, 2.80 mmol, 1.0 M in THF) was added dropwise and the reaction mixture was stirred at 25° C. for 4 h. The resulting mixture was concentrated in vacuo and the residue was purified with a Biotage column chromatography system on silica gel with a hexanes:ethyl acetate (8:2 to 7:3) gradient as the eluent to afford the title compound as a white solid (0.36 g, 58% yield): 1H NMR (400 MHz, CDCl3) δ: 8.06 (1H, d, J=1.0 Hz), 7.90 (1H, d, J=1.3 Hz), 7.76 (1H, dd, J=8.8, 5.3 Hz), 7.39 (1H, dd, J=8.3, 2.8 Hz), 7.19 (1H, ddd, J=8.9, 7.5, 3.0 Hz), LCMS (+ESI, M+H+) m/z 242/244.

1. concentrationThe resulting mixture was concentrated in vacuo
2. customthe residue was purified with a Biotage column chromatography system on silica gel with a hexanes:ethyl acetate (8:2 to 7:3) gradient as the eluent

ORD record

ord-de306768731040d894e6080c6e2da83c

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039458B2