Ammonium Chloride → HCID 67458542, compound

Participants

Reaction Steps

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 11.57 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (4.4 g, 16.72 mmol) in THF (168 mL) at −78° C. and the mixture solution was stirred at the same temperature for 15 minutes. To this solution, a solution of 4-bromobenzaldehyde (2.47 g, 13.34 mmol) in THF (50 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 30 minutes and at 0° C. for 30 minutes, 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 (1:10)] to obtain the title compound (4.08 g, 83%) as a colorless oil.

Provenance & Evidence