Hydrochloric Acid → 1,2-bis(4-iodophenyl)ethane-1,2-dione

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Reaction Steps

Under N2, benzotriazol-1-yl-(4-iodo-phenyl)-methanone (JYC-II-056-A) (3.5 g, 10.0 mmol) dissolved in 40 mL of anhydrous THF was added to a THF solution of SmI2 (221 mL of 0.1 M solution in THF, 22.1 mmol) at room temperature. The resulting mixture turned yellow brown in 5 min. HCl (2M, 65 mL) was added and the mixture was extracted with diethyl ether several times. The combined organic layers were washed with brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was washed with MeOH to give a yellow solid (0.73 g, 31.5%). 1H NMR (300 MHz, CDCl3, δ): 7.88 (d, J=8.5 Hz, 4H), 7.64 (dt, J=8.8 Hz, 4H). HRMS-EI (m/z): [M]+ calcd for C14H8I2O2, 461.86138; found, 461.86180.

Provenance & Evidence