Pyridine → 2-(1-Chloro-indan-5-yl)-benzonitrile

Participants

Reaction Steps

To a solution of 2-(1-hydroxy-indan-5-yl)-benzonitrile (3.3 grams, 14 mmol) and pyridine (2.4 mL, 30 mmol)in CH2Cl2 (30 mL) at 0° C. was added thionyl chloride (3.3 grams, 2.04 mL, 28 mmol). The reaction mixture was allowed to warm slowly to room temperature. After 1 hour, the reaction mixture was cooled to 0° C., quenched with saturated aqueous NaHCO3 (10 mL) and diluted with methylene chloride (CH2Cl2) (100 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL), dried (MgSO4) and concentrated in vacuo to give a yellow oil. 1H NMR (250 MHz, CDCl3): d 7.78 (1H, d), 7.65 (1H, t), 7.48 (m, 5 H), 5.48 (dd, 1 H), 3.25 (m, 1 H), 2.98 (m, 1 H), 2.67 (m, 1 H), 2.45 (m, 1 H).

Provenance & Evidence