5-BROMO-2(3H)-BENZOTHIAZOLONE

White crystalline

To a solution of2-amino-4-bromobenzenethiol (544 mg, 2.67 mmol)in acetic acid (26.7mL)was added triphosgene (530 mg, 1.79 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature, the solution was partially concentrated under reducedpressure, water was added, and the resulting precipitate was removed via filtration, and washed with aqueous NaOH (1.0 M). The filtrate was acidified with HCl (2 N)to pH 2, and placed in arefrigerator for 12 h. The resulting precipitate was filtered, washed with water, and dried underreduced pressure to give the title compound (94 mg, 15percent)as a while powder that required nofurther purification. 1H NMR (400 MHz, DMSO-d6)8 12.07 (s, 1H), 7.55 (d, J = 8.4 Hz, 1H), 5 7.30 (d, J = 8.0 Hz, 1H), 7.24 (s, 1H).Zn (70 g, 1077 mmol) was added to a solution of B (28 g, 120 mmol) in AcOH (500 ml). Reaction mixture was stirred at 65°C for 15 h under nitrogen to give C, monitored by TLC. The mixture was cooled to room temperature, and triphosgene (25 g, 84 mmol) added slowly at 0°C. Mixture was refluxed for 18 h, monitored by TLC. Solution was then concentrated and hydrolyzed with water. Yellow solid was collected to give D (20 g, 73percent, over two steps).

Molecular Weight:230.08
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:228.91970
Monoisotopic Mass:228.91970
Topological Polar Surface Area:54.4
Heavy Atom Count:11
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes