Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile

Participants

Reaction Steps

To a solution of 2-chloro-4-hydroxybenzonitrile 11 (10.0 g, 65.1 mmol) in CH3CN (200 mL) were added triflic acid (10 mL, 71.6 mmol), NBS (16.2 g, 91.2 mmol) at −30° C. The mixture was warmed-up to room temperature and stirred at room temperature for 15 h. The reaction was quenched by addition of aq. saturated NaHSO3 solution. The mixture was extracted with EtOAc. The combined organic extract was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 12 (9.8 g, 65%).

Provenance & Evidence