Iodine → HCID 15753779, compound

Participants

Reaction Conditions

Reaction Steps

1.05 g (39 mmol) of aluminum flakes, a spatula tipful of mercury chloride and an iodine crystal are warmed at 40° C. for one hour in 5 ml of absolute tetrahydrofuran under a nitrogen atmosphere. The mixture is heated to 60° C. and 6.9 g (58 mmol) of propargyl bromide in 10 ml of absolute tetrahydrofuran are added dropwise. The mixture is subsequently stirred at 60° C. for 60 minutes and then cooled to -60° C. A solution of 10 g (29 mmol) of 1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-(1,2,4-triazol-1-yl)-ethan-1-one in 20 ml of absolute tetrahydrofuran is then added dropwise and the mixture is subsequently allowed to react first for 1 hour at 0° C. and then for 2 hours at room temperature. 20 ml of a saturated aqueous ammonium chloride solution are added, the precipitate obtained is filtered off with suction, and the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate, and the resulting solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. In this manner, 8.8 g (80% of theory) of 4-(2-chloro-4-(4-chlorophenoxy)-phenyl)-5-(1,2,4-triazol-1-yl)-pent-1-yn-4-ol are obtained in the form of a solid of melting point 124° C.

Provenance & Evidence