Diethyl Ether → 3-(2-Bromo-phenoxy) acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 972 mg (11.56 mmol) of ethyl propiolate in 20 mL of THF at 0° C. is added a solution of 1.61 mL (11.56 mmol) of triethylamine in 5 mL of THF, followed by a solution of 2.0 g (11.56 mmol) of 2-Bromophenol in 5 mL of THF. The resulting clear orange-brown solution is stirred 5 h at 0° C., then poured into 100 mL of Et2O and extracted with H2O (1×100 mL). The organic layer is separated and washed with sat. Na2CO3 (1×100 mL), dried (MgSO4), and the solvent removed in vacuo to provide 2.97 g of the title compound as an orange oil which is used without any further purification: 1H NMR (CDCl3, 300 MHz) δ7.71 (d, 1H, J=12.3), 7.61 (d, 1H, J=7.4), 7.37-7.08 (m, 3H), 5.47 (d, 1H, J=12.3), 3.72 (s, 3H); Rf =0.40 in hexane/EtOAc 5/1.

Provenance & Evidence