1,3-Dibromobutane → Racemic ethyl 1-(3-bromobutyl)cyclobutanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of DIPA (14.3 mL, 102 mmol) in THF (100 mL) was added n-BuLi (2.5M, 102 mmol). The Rx was stirred for 30-45 min then cooled to −78° C. Ethyl cyclobutane carboxylate (102 mmol, 1 equiv) was added slowly and the enolate was allowed to form for ˜30 min. At ˜78° C., above enolate was poured into 1,3-dibromobutane (2 equiv, 200 mmol) and Rx stirred at −78° C. for 1 h then warmed-up to RT. After 3 hours, NH4Cl was added and reaction extracted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered and concentrated down to give 25 g of crude product. The residue was purified by silica gel chromatography (0% to 10% EtOAc in hexanes) to provide 11 g (42% yield) of racemic ethyl 1-(3-bromobutyl)cyclobutanecarboxylate 92.

Provenance & Evidence