Cesium carbonate → 2-Chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

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Reaction Steps

To the solution of 2H-1,2,3-triazole (CAS number 288-36-8; 4.0 g, 57.97 mmol) in DMF (14 ml) was added cesium carbonate (18.84 g, 57.97 mmol), trans-1-N,2-N-dimethylcyclohexane-1,2-diamine (0.510 g, 5.80 mmol), copper(I) iodide (0.276 g, 1.45 mmol) and 2-bromo-6-chlorobenzoic acid (CAS number 93224-85-2; 6.78 g, 28.98 mmol) at 0-10° C. The reaction was subjected to microwave irradiation at 125° C. for 15 minutes and was then partitioned between ethyl acetate (3×100 ml) and water (100 ml). The aqueous layer was acidified with 2M HCl (aq) to give pH 2 and then extracted with ethyl acetate (3×100 ml). The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was then purified by column chromatography (0-3% methanol/DCM) to afford the title compound.

Provenance & Evidence