Boron tribromide → HCID 68516960, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-(2-{4-[6-methoxy-2-(2-methyl-4-methylsulfanyl-phenyl)-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine hydrochloride (331 mg, 0.603 mmol) in dichloromethane (15 mL) and cool to 5° C. Add BBr3 (285 μL, 3.02 mmol) to the light suspension over 5 minutes. Quench the reaction after 1 hour with saturated aqueous NaHCO3 (15 mL). Separate the layers and extract the aqueous layer with dichloromethane (2×10 mL). Pour the solution onto a SiO2 plug (20 g) and elute with methanol in dichloromethane (5 to 15%). Concentrate the fractions in vacuo to give 301 mg of the title compound (100%): mass spectrum (ion spray) m/z=500.3 (M+H).

Provenance & Evidence