Azobisisobutyronitrile → HCID 68506530, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-fluoro-5-methylbenzonitrile, AIBN (0.1 eq.) and NBS (1 eq.) in CCl4 (0.14 M) was stirred at 80° C. for 18 h. After cooling to RT the mixture was quenched with 1N aq. NaS2O3 and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness under reduced pressure. The residue was dissolved in MeCN (0.2 M), then trimethylsilyl cyanide (1 eq.) was added, followed by TBAF (1M in THF, 1 eq.). The mixture was stirred for 2 h at RT, and then water was added and the solvents were removed under reduced pressure. The residue was diluted with DCM, washed with brine, dried (Na2SO4), and concentrated to dryness under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 5-50% EtOAc/petroleum ether to afford the product as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.78 (1H, d, J=6.3 Hz), 7.55 (1H, d, J=7.8 Hz), 3.82 (2H, s). MS (ES) C9H4BrFN2 requires: 238/240, found: 237/239 (M−H)−.

Provenance & Evidence