Boron tribromide → 3-(6-Fluoro-benzo[d]isoxazol-3-yl)-phenol

Participants

Reaction Conditions

Reaction Steps

Combine 6-fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole (30 g, 0.123 mol) and dichloromethane (anhydrous, 360 mL) under nitrogen atmosphere and cool (0° C.). Slowly add 1.0 M solution of boron tribromide in dichloromethane (370 mL, 0.370 mol) over 1 hour and stir at 0° C. for 3 hours. TLC indicates that all starting material is consumed. Quench the reaction mixture with 150 mL methanol, concentrate and azeotrope off the boron tribromide two more times with methanol. Dissolve the material in ethyl acetate, wash with K2CO3, saturated sodium chloride, dry (MgSO4) and concentrate. Triturate in heptane:dichloromethane (9:1), filter and wash with heptane and dry in the oven to give the title compound (26.93 g, 95% Yield). NMR and microanalysis (C, H, N) are consistent with the final, desired compound. mp=144-145° C.

Provenance & Evidence