Benzene → HCID 66627125, compound

Participants

Reaction Conditions

Reaction Steps

Inside a glove box, a 125 mL round-bottom flask equipped with a stirring bar, reflux condenser, and gas inlet was charged with 4,4′-dichlorobiphenyl-2,2′-disulfonyl dichloride (15.4 g, 36.7 mmoles), benzene (25 mL, 280 mmoles), and anhydrous nitromethane (75 mL). Aluminum chloride (11 g, 81 mmoles) was added and the mixture stirred until dissolved under nitrogen. The solution was heated to 100° C. for 8 hours. The solution was cooled to room temperature and poured onto 200 g ice mixed with 100 mL hydrochloric acid. The mixture was extracted several times with dichloromethane. The organic extracts were washed with water, dried with sodium carbonate, filtered to give a dark solution. The solution was treated with decolorizing carbon and heated to a reflux, then filtered through filter aid, evaporated, and the solids dried at 150° C. in a vacuum oven for 8 hr to give 18.02 g (97% crude yield). The mixture was purified by column chromatography using silica gel and dichloromethane (Rf 0.28) to give 14.3 g (77% yield) of 2,2′-bis-benzenesulfonyl-4,4′-dichlorobiphenyl. The solids were recrystallized from xylenes to give 13.08 g (71%). 1H NMR (DMSO-d6): 6.96 (d, 8.2 Hz, 2H), 7.55 (bs, 4H), 7.56 (m, 8.1 Hz, 4H), 7.69 (m, 2H), 7.74 (dd, 8.2, 2.2 Hz, 2H), 8.13 (d, 2.2 Hz, 2H). 13C NMR (CDCl3): 128.42 (4CH), 129.14 (4CH), 129.58 (2CH), 132.21 (2CH), 133.84 (2CH), 134.13 (2CH), 134.68 (2C), 135.61 (2C), 140.42 (2C), 141.42 (2C). MS (M+H+): m/e 502.99 (100%), 504.99 (75%), exact mass for C24H17O4Cl2S2, 502.99 (100%), 504.99 (72.9%).

Provenance & Evidence