N-bromobutanimide → (4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

To a stirred solution of (4-benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (350 mg, 1.08 mmol) in acetonitrile (10 mL) was added N-bromosuccinimide (385 mg, 2.16 mmol). After being stirred at room temperature for 1 hour, the resulting mixture was diluted with water (20 mL), and extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with water (15 mL) and brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 0-20% ethyl acetate in hexanes) to afford (4-benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (400 mg, 92%) as a white solid.

1. extractionextracted with ethyl acetate (20 mL×2)
2. washThe combined organic layers were washed with water (15 mL) and brine (20 mL)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography (gradient elution with 0-20% ethyl acetate in hexanes)

ORD-Eintrag

ord-7989ccab2fcb458eaa15406f65fa5fbd

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08642629B2