2-(4-Bromomethyl)phenylpropionic acid

Chemical Properties

beige-cream crystalline powder

Uses

2-[4-(Bromomethyl)phenyl]propionic Acid is a key intermediate for the synthesis of loxoprofen sodium a nonsteroidal anti-inflammatory drug.

General Description

2-[4-(Bromomethyl)phenyl]propionic acid is a propionic acid derivative. Its enthalpy of vaporization at boiling point (421.15K) is 36.363kjoule/mol and density at 25°C is 1.4212g/ml.

Synthesis

The synthesis method comprises the following steps: dissolving sodium hydroxide in excessive methanol to react with p-chloro-tolualdehyde to obtain p-methoxy-tolualdehyde, andthen performing chloromethylation reaction on the p-methoxy tolualdehyde and concentrated hydrochloric acid in the existence of sulfuric acid to obtain p-chloromethyl benzyl ether; performing nucleophilic reaction on the p-chloromethyl benzyl ether and the sodium cyanide to obtain p-methoxy-methyl benzyl cyanide; reacting the p-methoxy-methyl benzyl cyanide with dimethyl carbonate under high pressure in the existence of a catalyst to obtain p-methoxy-methyl benzyl iso-propionitrile; and reacting the p-methoxy-methylbenzyl sodium isopropionate with excessive concentrate sulfuric acid to generate molten salt which is reacted with hydrobromic acid to obtain 2-(4-Bromomethyl)phenylpropionic acid.