Acetonitrile → HCID 68183036, compound

Participants

Reaction Conditions

Reaction Steps

4-(3,4-Dichlorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene (3.25 g, 11.5 mmol), 1,4-dioxane (93 mL), acetonitrile (93 mL), water (100 mL), copper(II) sulfate pentahydrate (11.46 g, 45.90 mmol), and potassium persulfate (12.41 g, 45.90 mmol) were combined in a round bottomed flask equipped with a stirbar. The mixture was stirred overnight at 90° C. under an atmosphere of nitrogen during which time the blue color of the reaction disappeared to leave a light brown solution with some light greenish solid. The reaction was cooled to rt then additional copper(II) sulfate pentahydrate (11.46 g, 45.90 mmol) and potassium persulfate (12.41 g, 45.91 mmol) were added and the reaction was stirred at 90° C. under an atmosphere of nitrogen for an additional 5 hours. The reaction was cooled to rt and quenched with a solution of saturated sodium bisulfite. Saturated NaHCO3 solution was added until the mixture was basic, then ethyl acetate was added, the biphasic mixture was transferred to a separatory funnel and the organic layer was separated. The aqueous layer was extracted with additional ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to leave crude product as darkish orange oil. The residue was purified using column chromatography on silica gel (330 g RediSep column, gradient 0% EA in hexane to 25% EA in hexane over 30 minutes) give the product 1.29 g (38% yield) product as a light tan solid. LCMS: (FA) ES+ 297, 299. 1H NMR (400 MHz, DMSO) δ 8.00-7.93 (d, J=5.0 Hz, 1H), 7.64-7.57 (d, J=8.3 Hz, 1H), 7.55-7.49 (d, J=2.1 Hz, 1H), 7.22-7.14 (dd, J=8.3, 2.1 Hz, 1H), 6.72-6.65 (d, J=5.0 Hz, 1H), 4.41-4.32 (dd, J=9.2, 4.8 Hz, 1H), 2.72-2.59 (m, 1H), 2.57-2.51 (m, 1H), 2.39-2.19 (m, 2H).

Provenance & Evidence