1,4-Dibromobenzene → 3-(4-Bromophenyl)oxetan-3-ol

Participants

Reaction Conditions

Reaction Steps

1,4-Dibromobenzene (2 g, 8.48 mmol) was taken up in THF (35 mL) and cooled to −78° C. before adding n-BuLi (3.39 mL, 8.48 mmol) dropwise. After stirring at −78° C. for 30 minutes, oxetan-3-one (0.611 g, 8.48 mmol) was added and the reaction was warmed to room temperature for 1 hour at which time water and saturated NH4Cl were added and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a white solid.

Provenance & Evidence