Methyl iodide → Methyl 3-(2-bromophenyl)propanoate

Participants

Reaction Steps

Methyl iodide (51 g, 22.4 ml, 0.24 mole) was added to a stirred mixture of 3-(2-bromophenyl)propanoic acid (36.7 g, 0.16 mole, prepared as described by F. G. Holliman and F. G. Mann J Chem. Soc. 9, 1960) and anhydrous potassium carbonate (33 g, 0.24 mole) in dry N,N-dimethylformamide (250 ml) and the mixture was stirred at ambient temperature overnight. After removal of the solvent in vacuo the residue was partitioned between ether and water and the ethereal phase washed with aqueous sodium thiosulphate and then brine and dried (MgSO4). Evaporation gave a pale yellow oil which distilled at 116°-118° C. (0.2 mm) to give 36.91 g (95%) of the title ester as a colourless oil, νmax 2950, 1740, 1570, 1470, 1440 cm-1, δ(CDCl3), 2.63 (2H, m, ArCH2), 3.07 (2H, m, CH2CO2), 3.70 (3H, s, CH3), 7.12 (3H, m, arom), 7.50 (1H, d, arom).

Provenance & Evidence