1,4-Dibromobenzene → 1-(4-Bromophenyl)cyclobutanol

Participants

Reaction Conditions

Reaction Steps

A flame dried flask under N2 was charged with 1,4-dibromobenzene (7.52 g, 31.9 mmol) and anhydrous THF (50 mL). The reaction mixture was cooled to −78° C. and 2.5 M n-BuLi in hexanes (12.8 mL, 32 mmol) was added keeping the temperature below −60° C. The reaction mixture was stirred-at −78° C. for 30 min and then cyclobutanone (2 mL, 26.8 mmol) was added slowly keeping the temp below −60° C. After one hour, the reaction was poured into a saturated NH4Cl solution (40 mL). The salts were filtered through Celite™ and washed with EtOAc (2×20 mL). The layers were separated and the aq. phase was extracted with additional EtOAc (20 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to a pale yellow oil (5.51 g). The material could be used without further purification. 13C NMR (400 MHz, CDCl3) d 145.5, 131.7, 127.1, 121.3, 76.8, 37.2, 13.2; MS (AP/Cl) 209.0, 211.0 (M+H—H2O)+.

Provenance & Evidence