Benzaldehyde → HCID 16735193, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromodiphenyl ether (2.0 g, 8.03 mmol) in TBF (15 mL) at −78° C. was added n-butyllithium (3.85 mL, 2.6 M solution in hexanes). The reaction was stirred under argon for 2 hrs before a solution of benzaldehyde (0.85 g, 8.03 mmol) in THF at −78° C. was added. After stirring at −78° C. for 2 hrs, the reaction was quenched with water and extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (15%/85%)) to give 127 (2.22 g, 97% yield): 1H-NMR (400 MHz, chloroform-d) δ 7.28-7.40 (m, 9H), 7.10 (t, J=7.6, 1H), 6.94-7.01 (m, 4H), 5.84 (d, J=3.6 Hz, 1H), 2.17 (d, J=3.6 Hz, 1H).

Provenance & Evidence