Methanol → HCID 135949498, compound

Participants

Reaction Steps

To a stirred solution of 3-(2-chloro-4-trifluoromethyl-phenyl)-5-(4-methoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine (3) (1.000 g, 2.7119 mmol) in anhydrous dichloromethane (20 ml), cooled to −78° C. and under a nitrogen flow, a solution of boron tribromide (11.5497 g, ˜4.36 ml, 46.1023 mmol) in 10 ml of anhydrous dichloromethane is added drop-wise. The mixture is allowed to reach room temperature spontaneously overnight and it is then cooled again in an ice-salt bath and the excess of the reagent is decomposed upon drop-wise addition of 10 ml of methanol and 10 ml of water. After 10 min stirring, 10% sodium hydroxide solution (20 ml) is added and the aqueous layer, once separated, is acidified with 10% hydrochloric acid solution and extracted with chloroform (3×70 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to afford a solid grey residue (0.800 g, 83% yield, 99.47% pure at HPLC). M.p. 161-162.3° C. LC-ESI-HRMS of [M+H]+ shows 355.0579 Da. Calc. 355.057348 Da, dev. 1.6 ppm.

Provenance & Evidence