2,1-Benzisoxazole,6-chloro-(8CI,9CI) synthesis

Yield: 80%

Reaction Conditions:

with tin(II) chloride dihdyrate in methanol;ethyl acetate at 25; for 20 h;

Steps:

6-Chlorobenzo[c]isoxazole (5b)
General procedure: A round bottom flask equipped with a magnetic stirrer bar was charged with the 2-nitroacylbenzene (1.00 mmol) in EtOAc-MeOH (1:1; 5 mL). SnCl₂.H₂O (3.00 mmol) was added and the reaction stirred at room temperature overnight. The reaction was partitioned between DCM (30 mL) and NaHCO3 (20 mL). The aqueous phase was extracted with DCM (3 × 10 mL) and the organic portions combined, washed with H2O (10 mL), saturated aqueous NaCl (10 mL), dried over MgSO4, filtered and reduced in vacuo. The residue was purified by column chromatography (SiO₂, hexane/EtOAc) to provide the title compound. General procedure gave the title compound as an orange solid (122 mg, 80%).

References:

Chauhan, Jay;Fletcher, Steven [Tetrahedron Letters,2012,vol. 53,# 37,p. 4951 - 4954] Location in patent:supporting information