Cesium carbonate → 5-chloro-4-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Cs2CO3 (742 mg, 2.28 mmol) was added portionwise to a RT solution of 2-bromo-5-chloro-4-methyl-benzoic acid methyl ester (300 mg, 1.14 mmol) in DMF (3 mL) followed by 1H-1,2,3-triazole (0.1 mL, 1.71 mmol), Cu(I)I (13 mg, 0.068 mmol) and DMCDA (40 μL, 0.23 mmol). The resulting suspension was heated to 120° C. for 4 h. The reaction mixture was cooled to RT, quenched with 2M aq. HCl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by prep. HPLC (method E) to give the title compound as a pale yellow solid. LC-MS A: tR=0.72 min; [M(35Cl)+H]+=238.01.

Provenance & Evidence