Iodoethane → Ethyl 2-(4-bromophenyl)butanoate

Participants

Reaction Steps

To a solution of ethyl 2-(4-bromophenyl)acetate (972 mg, 4 mmol) in 10 mL dry THF at −78° C. was added LDA (2 M, 2 mL, 4 mmol). The solution was warmed to rt and stirred 2 h, then was recooled to −78° C. EtI (0.52 mL) was added, then the reaction was stirred rt for 16 h. The reaction was quenched with sat. NH4Cl, then extracted with EtOAc (3×20 mL). The organic layer washed with brine, then dried (Na2SO4). Purification via flash chromatography (0-20% EtOAc in hexanes) gives 75A (228 mg, 21%). MS (ESI) m/z 271.0 (M+H)+.

Provenance & Evidence