Boron tribromide → 2-hydroxy-N,N,2-tri(4-hydroxyphenyl)propanamide

Participants

Reaction Steps

2-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide (0.60 g, 1.47 mmol) was to dissolved in 30 mL of anhydrous methylene chloride in a dry 250 mL round-bottomed flask fitted with a stiffing bar, anitrogen inlet and rubber stopper. BBr3 solution (6.00 mL of 1M CH2Cl2 solution, 6.00 mmol) was added dropwise with stiffing at 0° C. The reaction solution was stirred at room temperature overnight. The reaction was quenched by adding 20 mL of water and extracted with EtOAc (3×30 mL). The EtOAc layers were separated and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica gel, CH2Cl2/MeOH=9/1 v/v) to give a white solid product, 2-hydroxy-N,N,2-tri(4-hydroxyphenyl)propanamide (11k), 0.42 g, 77.8% yield.

Provenance & Evidence