2-Bromobenzonitrile → 2-(1-Oxo-indan-5-yl)-benzonitrile

Participants

Reaction Steps

A mixture of 5-tributylstannanyl-indan-1-one (2.25 grams, 5.8 mmol), 2-bromobenzonitrile (1.06 grams, 5.8 mmol) and PdCl2 (PPh3)2 (421 mg, 0.6 mmol) was heated in dioxane (15 mL) for 20 hours. The reaction was cooled to room temperature, concentrated in vacuo and transferred to a SiO2 -gel column. Flash chromatography using a gradient of 25% ethyl acetate/hexanes to 50% ethyl acetate/hexanes yielded 725 mg of a colorless solid. 1H NMR (250 MHz, CDCl3): d 7.9 (d, 1 H), 7.8 (d, 1 H), 7.69 (m, 2 H), 7.54 (m, 3 H), 3.24 (t, 2 H), 2.78 (t, 2 H).

Provenance & Evidence