Ammonium Chloride → HCID 67461295, compound

Participants

Reaction Steps

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 3.14 mL) was added dropwise to a solution of 2-benzyloxy-1-bromo-4-fluorobenzene (1.4 g, 5.0 mmol) in THF (50 ml) at −78° C. and the mixture was stirred at the same temperature for 15 minutes. To this solution, a solution of 4-methoxybenzaldehyde (680 mg, 4.99 mmol) in THF (15 mL) was added dropwise at −78° C. and 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. The obtained residue was purified by silica gel column chromatography [developing solution=n-hexane:dichloro-methane:acetone (12:3:1)] to obtain the title compound (1.41 g, 83%) as a colorless oil.

Provenance & Evidence