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

To a solution of triphenylphosphine (37.2 g, 142 mmol) in dry THF (160 mL) was added CCl4 (50 mL). The reaction mixture was stirred for 10 minutes and (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (20.0 g, 70.8 mmol) was introduced as a solid at room temperature under nitrogen. The resulting solution was refluxed for 2 hours. THF was distilled off under reduced pressure, and the remaining material diluted with water (100 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained crude product was purified over silica gel column chromatography (100-200 mesh, 5% ethyl acetate in hexanes) to yield compound 1-benzyloxy-3-chloromethyl-7-fluoro-naphthalene (19.3 g, 90.6%) as a white solid.

1. temperatureThe resulting solution was refluxed for 2 hours
2. distillationTHF was distilled off under reduced pressure
3. additionthe remaining material diluted with water (100 mL)
4. extractionextracted with ethyl acetate (2×150 mL)
5. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe obtained crude product
9. customwas purified over silica gel column chromatography (100-200 mesh, 5% ethyl acetate in hexanes)

ORD record

ord-90e04585fa97431993d57e5bb76559a5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691993B2