Benzene → HCID 23154691, compound

Participants

Reaction Conditions

Reaction Steps

A modification of the published procedures of Hagberg, Olson, and Sheares in Macromolecules, 2004, 37, 4748 was used. A 200 mL round-bottom flask equipped with a reflux condenser, stirring bar, and gas inlet was charged with 2,5-dichlorobenzenesulfonyl chloride (12.28 g, 50 mmoles), benzene (13.4 mL, 150 mmoles), and anhydrous nitromethane (50 mL). Aluminum chloride (7.33 g, 55 mmoles) was added and the mixture stirred until dissolved under nitrogen. The solution was heated to 100° C. overnight. The solution was cooled to room temperature and poured into 100 g water mixed with 25 mL hydrochloric acid. The mixture was extracted several times with dichloromethane. The organic extracts were dried with sodium sulfate, filtered, and evaporated, then the solids were dried in a vacuum oven to give 14.38 g (100% crude yield). The solids were recrystallized from ethanol after treating with decolorizing carbon to give about 14 g in two crops. The solids were recrystallized from ethanol to give 12.24 g (85% yield) of 2-benzenesulfonyl-1,4-dichlorobenzene. 1H NMR (DMSO-d6): 7.65 (ddd, 8.4, 7.5, 1.7 Hz, 2H), 7.67 (d, 8.6 Hz, 1H), 7.76 (tt, 7.5, 1.2 Hz, 1H), 7.83 (dd, 8.6, 2.6 Hz, 1H), 7.98 (ddd, 8.4, 1.7, 1.2 Hz, 2H), 8.27 (d, 2.6 Hz, 1H).

Provenance & Evidence