Sodium hydride → Methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester

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Reaction Steps

Add sodium hydride (24 g, 0.6 mmol) portionwise to a solution of 6-benzyloxy-2-bromo-naphthalen-1-ol (179 g, 0.54 mol) in THF (3.0 L) at 0° C. Add methanesulfonyl chloride (47 mL, 0.61 mol) over 45 minutes and stir the reaction for 1.5 hours at 10° C. Add sodium bicarbonate solution (500 mL) and water (500 ml). Separate the layers and extract the aqueous layer with ethyl acetate (500 mL×2). Combine the organic layers and wash with brine (200 mL). Dry with magnesium sulfate, filter and concentrate in vacuo. Triturate the residue by adding 20% ethyl acetate in hexane (1 L) to obtain a solid. Filter, wash the solid with toluene (200 mL×2) and dry the solid to get 176 g (80%) of methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester.

Provenance & Evidence