Thionyl Chloride → 2-(2-Chloromethyl-benzo[b]thiophen-6-yloxy)-benzothiazole

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution [6-(benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanol (256 mg, 0.8 mmol) in DCM (8 mL) was added thionyl chloride (60 μL, 98 mg, 0.8 mmol) and the reaction mixture was stirred (0° C., 2 h). The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×20 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-40%) to provide the title compound as yellow solid (0.17 g, 65%). MS (ESI): mass calcd. for C16H10ClNOS2, 331.0; m/z found, 332.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.84 (d, J=2.2, 1H), 7.78 (d, J=8.7, 1H), 7.74 (dd, J=8.1, 0.6, 1H), 7.68 (dd, J=8.0, 0.7, 1H), 7.43-7.26 (m, 4H), 4.86 (s, 2H).

Provenance & Evidence