Methyl iodide → 2-Propenoic acid, 3-(4-bromophenyl)-, methyl ester

Participants

Reaction Steps

Anhydrous potassium carbonate (20.7 g, 0.15 mmole) was added to a solution of 4-bromocinnamic acid (22.7 g, 0.1 mmole) in dry N,N-dimethylformamide (150 ml) and the mixture was stirred for 30 minutes. Methyl iodide (21.3 g, 9.4 ml, 0.15 mmole) was then added and the total mixture stirred for a further 24 hours at room temperature before the solvent was evaporated in vacuo. Water was added to the residue and the product extracted into ether. The ethereal extracts were washed with saturated aqueous sodium bicarbonate solution, the brine and dried (MgSO4). Evaporation afforded 22.73 g (94%) of the ester as a white solid of mp (methanol) 82°-86° C. (lit mp 80° C., Dictionary of Organic Compounds), υmax (mull), 1718, 1640, 1595, 1495 cm-1. δ(CDCl3) 3.80 (3H, s, ester CH3), 6.37 (1H, d, J 13 Hz, =CHCO2), 7.42 (4H, m, arom), 7.62 (1H, d, J 13 Hz, ArCH=).

Provenance & Evidence