Acetic Acid → 6-Bromo-2-(methylsulfanyl)-1,3-benzothiazole

Participants

Reaction Steps

To the solution of 2-(methylthio)-1,3-benzothiazole (5.00 g, 27.58 mmol) in CHCl3 (85 mL) in a NaCl-ice water bath, bromine (4.24 mL, 82.8 mmol) was slowly added dropwise, followed by acetic acid (30 mL). The mixture was stirred at rt overnight. The white solid was filtered and then dissolved in EtOAc (200 mL). Saturated, aqueous Na2CO3 (200 mL) was added and the organic layer was separated, dried over MgSO4 and concentrated to dryness. Desired product (5.0 g, 70%) was obtained. 1H NMR (400 MHz, DMSO-d6) δ8.30 (s, 1H), 7.76 (d, 1H), 7.59 (d, 1H), 2.79 (s, 3H); LC-MS m/z [M+H]+ 260.2 & 262.1, RT 3.65 min.

Provenance & Evidence