Hydrochloric Acid → 5-Nitro-1-benzothiophene

Participants

Reaction Conditions

Reaction Steps

Copper (8.18 g, 0.129 mol) was added to a mechanically stirred slurry of 5-nitrobenzo[b]thiophene-2-carboxylic acid (28.73 g, 0.129 mol) and quinoxaline (160 mL). The thick mixture was heated to 190° C. Upon heating, stirring became easier, and at around 170° C. gas evolution was observed. Gas evolution ceased after 40 min and the reaction mixture was allowed to cool to r.t. overnight. The mixture was then poured over crushed ice and acidified with concentrated hydrochloric acid. The resulting brown suspension was warmed with diethyl ether (4×400 mL). The ether layers were combined, washed with 2 N aqueous hydrochloric acid (300 mL), water (300 mL) and brine (300 mL), and then separated, dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude yellow solid (26 g) was recrystallized from hot acetone (175 mL) to yield 5-nitrobenzo[b]thiophene (15.58 g, 68%) as pale yellow crystals. 1H NMR δ (d6-DMSO, 400 MHz) 7.63 (d, J=5.5 Hz, 1 H), 7.95 (d, J=5.5 Hz, 1 H), 8.08 (dd, J=9, 2 Hz, 1 H), 8.20 (d, J=9 Hz, 1 H), 8.75 (d, J=2 Hz, 1 H).

Provenance & Evidence