Cyclohexene → HCID 178418484, compound

Participants

Reaction Steps

A 1 L 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen bubbler was charged with 12.97 g (46.9 mmol) of 2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran and 500 mL of 1,4-dioxane. To the well-stirred solution at room temperature was added a solution of 4.8 mL (93.2 mmol) of bromine in 35 mL of carbon tetrachloride dropwise over 1 hour. Cyclohexene (16 mL) was added to the reaction mixture then it was concentrated under vacuum to an oily residue that was partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether. The aqueous layer was removed, acidified with 50 mL of 2N aqueous hydrochloric acid, and extracted several times with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum to give a white foam that was triturated with 100 mL of hot toluene. The mixture was cooled in an ice bath and the solids removed by filtration then washed with cold toluene, air dried and dried under vacuum to give 14.11 g (39.7 mmol, 85%) of product. 1H NMR (200 MHz,CDCl3 +1 drop DMSO-d6): 2.44 (s,3H), 7.1-7.3 (m,4H), 7.6 (m,2H), 7.86 (m,1H), 7.95 (m,1H).

Provenance & Evidence