Boron tribromide → HCID 22742097, compound

Participants

Reaction Steps

Boron tribromide (1.0 M solution in dichloromethane, 110 ml, 0.11 mol) was added dropwise to a stirred solution of N-(4-chloro-3-methylisothiazol-5-yl)-2-(4-methoxyphenyl)propionamide (125 g, 0.040 mol) in dichloromethane (200 ml) at −70° C. Once the addition was complete the cooling bath was removed and the mixture was allowed to warm to room temperature overnight. The mixture was cooled to 0° C. and excess methanol added cautiously. The solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo to give N-(4-chloro-3-methylisothiazol-5-yl)-2-(4-hydroxyphenyl)propionamide (11.8 g), which was used without further purification in the next step.

Provenance & Evidence