Methyl 4-bromobenzoate → Methyl 4-cyclobutylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of ZnBr2 (83.0 g, 369 mmol) in THF (500 mL) under nitrogen at 0° C. was added a solution of bromo(cyclobutyl)magnesium (242 mL, 363 mmol, 1.5 M in THF) dropwise over 20 min. The resulting mixture was cooled to −40° C. and Pd(dppf)Cl2 (2.00 g, 2.73 mmol) and methyl 4-bromobenzoate (20.0 g, 93.0 mmol) were added. The resulting mixture was stirred at -40° C. for 1 h under nitrogen, and then carefully quenched with saturated aqueous NH4Cl (500 mL). The mixture was extracted with ethyl acetate (3×500 mL) and the combined organic layers were washed with brine (3×500 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a light yellow oil (18.0 g, crude).

Provenance & Evidence