Hydrochloric Acid → 4-(4-Hydroxy-3-iodophenyl)benzonitrile

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Reaction Conditions

Reaction Steps

4′-Hydroxy-1,1′-biphenyl-4-carbonitrile (25.0 g, 128 mmol), purchased commercially, NaI (19.19 g, 128 mmol), and sodium hydroxide (5.12g, 128 mmol) were combined in methanol (500 mL) at 0° C. and treated with bleach (5.25%, 181.0 g) dropwise over 1 hour. After stirring at 0° C. for 1 hour, the mixture was treated with 10% aqueous sodium thiosulfate (250 mL). The mixture was adjusted to pH 6.8 with 10% aqueous HCl and then the mixture was filtered. The filter cake was crystallized from hot CH2Cl2/hexane to provide the title compound (40% yield). 1HNMR (300 MHz, CDCl3) δ5.40 (s, 1H), 7.10 (m, 1H), 7.50 (m, 1H), 7.60 (m, 2H), 7.77(m, 2H), 7.90 (m, 1H); MS (CDI) m/z 339 (M+NH4)+.

Provenance & Evidence