Carbon Tetrachloride → 1-Benzyloxy-3-chloromethyl-7-fluoro-naphthalene

To a solution of triphenylphosphine (2.8 g, 10.6 mmol) in anhydrous tetrahydrofuran (16 mL) was added carbon tetrachloride (5 mL). After the mixture was stirred at room temperature for 10 minutes, (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (1.5 g, 5.3 mmol) was added as a solid under a nitrogen atmosphere. After being stirred at reflux for 2 hours, the resulting mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL×2). The combined aqueous layers were extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether) to afford 1-benzyloxy-3-chloromethyl-7-fluoro-naphthalene (1.4 g, 87.5%) as a white solid.

1. stirringAfter being stirred
2. temperatureat reflux for 2 hours
3. temperaturethe resulting mixture was cooled to room temperature
4. extractionextracted with ethyl acetate (100 mL)
5. washThe organic layer was washed with water (50 mL×2)
6. extractionThe combined aqueous layers were extracted with ethyl acetate (100 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether)

ORD record

ord-da10d871b004402bafe1777b24845d77

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188090B2