Pyridine → HCID 13235820, compound

Participants

Reaction Steps

A solution of bromine (1.28 g) in dichloromethane (25 ml) was added dropwise over 15 minutes to a stirred solution of 2-(4-chlorophenyl)-5-hydroxyoct-1-ene (1.9 g) and pyridine (0.63 g) in dichloromethane (25 ml) at 0° to 5° C. (decolourisation of bromine and mild exotherm). The cooling bath was removed and the mixture was stirred for a further 30 minutes, then washed successively with water, dilute hydrochloric acid, aqueous sodium bicarbonate, and water, then dried over magnesium sulphate and concentrated under reduced pressure to give 2-(4-chlorophenyl)-2-bromomethyl-5-prop-1-yltetrahydrofuran (2.6 g) as a red oil, 1H nmr (CDCl3): δ3.9 (2H, singlet, CH2Br).

Provenance & Evidence