Diethyl Ether → HCID 67216472, compound

Participants

Reaction Steps

Subsequently, 9.67 g (28.2 mmol) of (methoxymethyl)triphenylphosphonium chloride and 48 mL of dry diethyl ether were charged into a 300-mL recovery flask filled with nitrogen at room temperature. The mixture was stirred. Then 28.2 mL (28.2 mmol) of 1 M tert-butoxypotassium solution in THF was added thereto. The resulting mixture was stirred for 1 hour. Subsequently, a solution of 3.90 g (11.3 mmol) of 1-bromo-4-(4-chloro-2-formylphenyl)naphthalene dissolved in 93 mL of a THF solvent was added to the reaction mixture. After the resulting mixture was stirred for another 4 hours at room temperature, water was added thereto, terminating the reaction. The separation of two phases was performed to recover the aqueous phase. Extraction of the aqueous phase was performed three times with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, and concentrated to give a crude product. The crude product was then purified by silica gel column chromatography (eluent: heptane/chloroform=20/1) to give 4.17 g (yield: 99%) of 1-bromo-4-(4-chloro-2-methoxyethenylphenyl)naphthalene.

Provenance & Evidence