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

Participants

Reaction Steps

To a solution of methyl 5-chloro-2-ethynylbenzoate (1.13 g, 5.8 mmol) in TBME (50 ml) was added Pd/C (10%) (50% water, 0.61 g, 0.29 mmol). The reaction mixture was stirred under a hydrogen atmosphere for 130 minutes. The mixture was filtered through Celite and the filter cake was washed with TBME. The filtrate was concentrated in-vacuo to give the title compound (1.08 g, 74%) as a pale brown oil. LC-MS 79%, m/z=198.9/200.9; 1H NMR (500 MHz, Chloroform-d) δ ppm 7.85 (s, 1H) 7.40 (d, J=8.20 Hz, 1H) 7.22 (d, J=8.20 Hz, 1H) 3.91 (s, 3H) 2.95 (q, J=7.46 Hz, 2H) 1.22 (t, J=7.49 Hz, 3H).

Provenance & Evidence