Benzyl Bromide → 4-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester

To a solution of 6-fluoro-4-hydroxy-naphthalene-2-carboxylic acid methyl ester (3.7 g, 16.8 mmol) in dry DMF (40 mL) was added K2CO3 (3.25 g, 23.5 mmol), benzyl bromide (3.44 g, 20.2 mmol) and Bu4NI (0.02 g) simultaneously at room temperature under nitrogen. The reaction mixture was stirred for 3 hours at room temperature. The mixture was diluted with water (60 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the crude product. Silica gel column chromatography (2%-5% ethyl acetate in hexanes) afforded 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (4.6 g, 88%) as an off-white solid. MS cald. for C19H16FO3 [(M+H)+]: 311, obsd. 311.0.

1. extractionextracted with ethyl acetate (2×100 mL)
2. washThe combined organic extracts were washed with water (30 mL), brine (30 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo
5. customto obtain the crude product

ORD record

ord-7b21e1f395954eefab4b3249891b037f

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691993B2