2-Bromo-6-methoxycarbonylnaphthalene → (6-Bromonaphthalen-2-yl)methanol

Participants

Reaction Steps

To a three-necked flask (5 L) cooled with an ice-bath was added lithium aluminum hydride (40 g, 1.05 mol), and anhydrous THF (500 mL) under nitrogen protection. To this suspension, Methyl 6-bromo-2-naphthoate (141 g, 0.534 mol) dissolved in anhydrous THF (1200 mL) was added dropwise slowly through a dropping funnel. Cooling bath was removed and the reaction mixture was kept under stirring for additional 2 hours. The reaction mixture was cooled with an ice-bath again, and to it was added methanol (150 mL) dropwise carefully until there was no gas release. The mixture was kept under stirring for half an hour and then was acidified with concentrated hydrochloric acid to a PH of about 4. The resulting solid was removed by filtering under reduced pressure and the filtrate was concentrated, and then poured into deionized water (2 L). The resulting precipitate was collected by suction filter, and washed with deionized water, followed by a little ethanol, and dried in vacuum to afford (6-bromonaphthalen-2-yl)methanol (95.4 g).

Provenance & Evidence