Iodine → HCID 58941090, compound

Participants

Reaction Steps

1-(4-Ethynylphenyl)piperidine (3.49 g, 18.8 mmol) in dry THF (100 mL) was added to a suspension of bis(cyclopentdienyl)zirconium(IV)chloride hydride (5.09 g, 19.76 mmol) in THF (50 mL) at r.t. under nitrogen in the dark. After 1 h, iodine (3.65 g, 23.7 mmol) was added. After a further 2 h, saturated aqueous sodium sulfite (50 mL) was carefully added and the reaction mixture was partitioned between water (30 mL) and EtOAc (100 mL). The organic layer was separated and dried (MgSO4), filtered and concentrated. Purification by column chromatography (5% EtOAc in PE) gave the title compound (3.08 g, 52%) as a colorless-solid. 1H NMR (CDCl3) 1.61 (2H, m), 1.70 (4H, m), 3.20 (4H, m), 6.54 (1H, d), 6.83 (2H, d), 7.19 (2H, d), 7.31 (1H, d).

Provenance & Evidence