Trichloroisocyanuric Acid → HCID 57912300, compound

Participants

Reaction Steps

An aqueous solution of 15% NaHCO3 (18 mL) was added to a stirring solution of Compound 9 (1.80 g, 2.69 mmol) in acetone (60 mL) at 0° C. NaBr (133 mg, 1.29 mmol) and TEMPO (18.9 mg, 0.121 mmol) were then added followed by the slow addition of trichloroisocyanuric acid (2.81 g, 12.1 mmol). The resulting solution was allowed to warm to room temperature and stirring for 1 d after which time 2-propanol (3.63 mL) was added. The mixture was filtered over Celite, concentrated on a rotary evaporator, dissolved in 18 mL of saturated Na2CO3, washed with EtOAc (3×10 mL), acidified with 1 M HCl, and extracted with ethyl acetate (3×50 mL). The resulting organics were dried over Na2SO4, filtered, concentrated on a rotary evaporator and purified by silica gel chromatography (10% MeOH:CH2Cl2) to yield Compound 10 (1.05 g, 56%) as a white solid.

Provenance & Evidence