Cesium carbonate → Methyl 4-cyano-3-(cyclobutyloxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-cyano-3-hydroxybenzoate (0.067 g, 0.38 mmol) in 2 ml of DMF was added cesium carbonate (0.2 g, 0.62 mmol), bromocyclobutane (0.051 g, 0.38 mmol), and the reaction mixture was heated at 60° C. and stirred at this temperature for 3 hrs. The reaction mixture was cooled to RT, poured into ice water, and extracted several times with ethyl acetate (3×20 ml). The organic solution was dried over Na2SO4, filtered, rotary evaporated to dryness then dried in vacuo to provide methyl 4-cyano-3-(cyclobutyloxy)benzoate (0.055 g, 63%). 1H NMR (400 MHz, CD3OD): 7.74 (d, 1H), 7.67 (d, 1H), 7.54 (s, 1H), 3.93 (s, 3H), 2.57-2.52 (m, 2H), 2.26-2.21 (m, 2H), 1.94-1.90 (m, 1H), 1.94-1.78 (m, 2H). MS (EI) for C13H13NO3: 232 (MH+).

Provenance & Evidence