Water → (2-Benzyloxyphenyl)-(4-chlorophenyl)methanol

In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 10.3 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (6.0 g, 22.8 mmol) in THF (228 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-chlorobenzaldehyde (2.67 g, 19.0 mmol) in THF (76 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for two hour and further more at 0° C. for one hour. Water 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. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)] to obtain the title compound (4.76 g, 77%).

1. stirringThe reaction mixture was stirred at the same temperature for two hour and further more at 0° C. for one hour
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. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)]

ORD-Eintrag

ord-3be195af5e074aafbb2df1231ee304ca

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08048897B2