Potassium Carbonate → Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(4-chloro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (400 mg, 1.48 mmol) in MeCN (5 mL) was added anhydrous K2CO3 (414 mg, 3 mmol) and the mixture was cooled to −30° C. To this mixture was added 2-bromo-5-nitro-1,3,4-thiadiazole (420 mg, 2 mmol). The reaction mixture was stirred at −30° C. for 5 h. The reaction was quenched by addition of ice and the mixture was extracted with EtOAc (3×5 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product as a yellow oil (430 mg). MS (ESI) m/z=400 [M+H]+.

Provenance & Evidence