Boron tribromide → 6-Decyl-3-methylthio-2-hydroxynaphthalene

Participants

Reaction Steps

A dichloromethane (50 ml) solution of 6-decyl-3-methylthio-2-methoxynaphthalene (compound (4)-64) (28 g, 81 mmol) was added to a dichloromethane solution of BBr3 (ca.2 M 70 ml, 140 mmol) at −78° C. The solution was stirred at room temperature for 12 hours. Ice (approximately 20 g) was added to the mixture. The reaction solution was extracted with dichloromethane (20 ml×3). The organic layers obtained by repeating the extraction three times were collected, washed with saturated saline water (30 ml×3), dried with MgSO4, and condensed. The residue was refined by column chromatography (silica gel, developed at dichloromethane:hexane=1:1), and recrystallized with hexane to obtain 6-decyl-3-methylthio-2-hydroxynaphthalene (18.1 g, 72%) as white crystals.

Provenance & Evidence