Hydrochloric Acid → HCID 18670055, compound

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Reaction Steps

A solution of 3,4-bis(phenylethynyl)nitrobenzene (2.5 g, 7.7 mmol), SnCl2 (7.3 g, 39 mmol, 5 eq.), and HCl (5 mL, 10 eq.) in THF (20 mL) was stirred at room temperature for 5 h. After neutralization with NaOH (1.0N solution), product was extracted with dichloromethane. Solvent was evaporated and the residue was purified by column chromatography on silica gel using chloroform as the eluent to yield 1.7 g (75%) of 3,4-bis(phenylethynyl)phenylamine as a brown oil. 1H NMR (300 MHz, CDCl3) δ 7.67-7.61 (m, 4H), 7.42-7.35 (m, 7H), 6.85 (d, J=2.4 Hz, 1H), 6.62-6.58 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 3.85 (broad, 1H). 13C NMR (68 MHz, CDCl3) δ 146.3, 132.9, 131.5, 131.2, 131.8, 128.3, 128.2, 127.7, 126.5, 123.7, 123.1, 117.3, 117.2, 115.1, 114.9, 92.8, 91.2, 88.9, 88.5. m/z (high res. ESI) 294.1283 (Calc. C22H16N 294.1283).

Provenance & Evidence