Hydrochloric Acid → 2-[(4-Fluorophenyl)methyl]phenol

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 4.9 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (2.04 g, 7.75 mmol) in THF (60 mL) at −78° C. and the mixture was stirred at the same temperature for 20 minutes. To this solution, a solution of 4-fluorobenzaldehyde (801 mg, 6.45 mmol) in THF (10 mL) was added dropwise at −78° C. The mixture was stirred at the same temperature for 1.5 hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure to obtain a crude product (2.35 g) of the title compound. To a solution of the obtained crude product in methanol (15 mL), a 20% palladium hydroxide catalyst (186 mg) was added and furthermore 2N—HCl (400 μL) was added thereto. The mixture was stirred under a hydrogen atmosphere for three hours, and then the catalyst was filtered. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (996 mg, 77%).

1. stirringThe mixture was stirred at the same temperature for 1.5 hours
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
4. dry with materialdried (anhydrous magnesium sulfate)
5. distillationthe solvent was distilled under reduced pressure
6. customto obtain a crude product (2.35 g) of the title compound
7. stirringThe mixture was stirred under a hydrogen atmosphere for three hours
8. filtrationthe catalyst was filtered
9. distillationThe solvent was distilled under reduced pressure
10. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

ORD record

ord-f67bb9e8c5994689bd901e1ad00c6a71

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048897B2