4-Bromobenzyl bromide → Ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA (1.2 eq) in THF at −78° C. was added ethyl cyclobutanecarboxylate (1 eq) and reaction mixture was warmed up to −40° C. for 10 min. The reaction was cooled back to −78° C. for 1 h, then 4-bromobenzyl bromide (1.1 eq) was added as a solid to the mixture. The reaction mixture was warmed to 0° C. in an ice bath. The reaction was quenched with a saturated solution of NH4Cl and extract 3× with ethyl acetate, dried with MgSO4 and evaporated to dryness. Flash chromatography with 95:5 hexanes:ethyl acetate afforded ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate.

Provenance & Evidence