Reaktion #641702

Reaktionsgleichung

ammonium chloride

n-butyllithium hexane

1-benzyloxy-2-bromo-4-fluorobenzene

4-methoxybenzaldehyde

→

title compound

Ausbeute 66.0%

(2-Benzyloxy-5-fluorophenyl)-(4-methoxyphenyl)methanol

Ausbeute 66.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at the same temperature for one hour
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with a saturated sodium chloride aqueous solution
4. 4
   Trocknendried (anhydrous magnesium sulfate)
5. 5
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
6. 6
   SonstigeThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Vorschrift

In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 2.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromo-4-fluorobenzene (1.5 g, 5.33 mmol) in THF (60 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-methoxybenzaldehyde (0.6 g, 4.42 mmol) in THF (20 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour, 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. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (0.98 g, 66%).

Quelle