Methyl 5-chloro-2-ethynylbenzoate → Methyl 5-chloro-2-ethylbenzoate

Participants

Reaction Steps

To a solution of methyl 5-chloro-2-ethynylbenzoate (5.34 g, 27 mmol) in ethyl acetate (135 ml) was added Pd/C (10%) (50% water, 2.92 g, 1.37 mmol). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. The mixture was filtered through Celite. The filter cake washed with EtOAc (50 ml) and the filtrate was concentrated under reduced pressure to give 5.12 g (94%) of the title compound as a brown oil which was suitable for use without any further purification. LC-MS 56%, m/z=198.9/200.9, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.84 (d, J=2.3 Hz, 1H), 7.39 (dd, J=8.3, 2.3 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 3.90 (s, 3H), 2.94 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

Provenance & Evidence