Hydrogen and halogen bonding in the haloetherification products in chalcone. Issue 3 (19th February 2019) - Asgarova, Aytan R.
Abstract : The reaction of 3‐(3, 5‐di‐ tert ‐butyl‐4‐hydroxyphenyl)‐1‐phenylprop‐2‐en‐1‐one with HCl or HBr in MeOH of EtOH leads to the haloetherification products 3‐(3‐ tert ‐butyl‐5‐halo‐4‐hydroxyphenyl)‐2‐halo‐3‐alkoxy‐1‐phenylpropan‐1‐ones. Both intermolecular hydrogen and halogen bonds were found in the crystal structures of the haloetherification products of chalcone. Abstract : Cooperative action of hydrogen and halogen bonding in the reaction of 3‐(3, 5‐di‐ tert ‐butyl‐4‐hydroxyphenyl)‐1‐phenylprop‐2‐en‐1‐one with HCl or HBr in alcohol medium under microwave irradiation (20 W, 80 °C, 10 min) allows the isolation of the haloetherification products (2 S, 3 S )‐3‐(3‐ tert ‐butyl‐5‐chloro‐4‐hydroxyphenyl)‐2‐chloro‐3‐ethoxy‐1‐phenylpropan‐1‐one, C21 H24 Cl2 O3, (2 S, 3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐methoxy‐1‐phenylpropan‐1‐one, C20 H22 Br2 O3, and (2 S, 3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐ethoxy‐1‐phenylpropan‐1‐one, C21 H24 Br2 O3, in good yields. Both types of noncovalent interactions, e.g. hydrogen and halogen bonds, are formed to stabilize the obtained products in the solid state.