The effects of ortho substituents on reactivity. I. The alkaline hydrolysis of substituted ethyl phenylacetates was written by Watkinson, J. G.;Watson, William;Yates, B. L.. And the article was included in Journal of the Chemical Society in 1963.SDS of cas: 2178-24-7 This article mentions the following:
Rates of hydrolysis of ethyl phenylacetate and 24 nuclear-substituted derivatives have been measured at 24.8° in aqueous ethanol (85.4% by weight of ethanol). All the ortho substituents examined retard hydrolysis, even the nitro group which from the para position greatly accelerates it. Measurements at other temperatures show that the low rates are associated with high activation energies, and that the pre-exponential factor of the Arrhenius equation does not vary with substituents beyond the limits of exptl. error. Comparison of the results with those obtained with aqueous acetone (56% by weight of acetone) and with aqueous ethanol of different compositions as solvents reveals that the effects of substituents, and in particular of ortho substituents, are affected by the solvent. It is therefore suggested that an important factor in the retarding influence of ortho substituents in the alk. hydrolysis of ethyl phenylacetates is steric interference with solvation of the transition state. In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7SDS of cas: 2178-24-7).
Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.SDS of cas: 2178-24-7
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary