Bromine → HCID 86655362, compound

Potassium thiocyanate (500 mg, 5.12 mmol) was suspended in acetic acid (10 mL) and the mixture was stirred at room temperature for 10 min. To the obtained solution was added a solution of N-[3-(4-amino-2-fluorophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide (500 mg, 1.28 mmol) in acetic acid (10 mL), and the mixture was further stirred at room temperature for 15 min. To the obtained solution was added dropwise slowly a solution of bromine (0.225 g, 1.41 mmol) in acetic acid (7.0 mL) and, after the completion of the dropwise addition, the mixture was stirred at room temperature for 14 hr. The resulting yellow insoluble material was filtrated, and washed with acetic acid. The filtrate and washing were combined and concentrated under reduced pressure. The obtained residue was suspended in ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogencarbonate solution (200 mL×2), water (200 mL) and saturated brine (200 ml), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (0.32 g, 57%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.