Phenethyl bromide → 2-Methyl-1-phenethyl-1H-pyrrole-3-carboxylic acid ethyl ester

Participants

Reaction Steps

To an ice/water bath cooled solution of 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (11.43 g) and (2-bromo-ethyl)-benzene (20.20 mL) in DMF (100 mL) was carefully added NaH (3.88 g, 60% suspension in mineral oil). The mixture was subsequently stirred at room temperature overnight, and cooled with ice/water bath again, another 20.20 mL of (2-brom-ethyl)-benzene and 3.88 of NaH were added to the reaction, which was allowed to stir for another 5 h; then the mixture was quenched by pouring into a mixture of ammonium chloride and ice/water, extracted with EtOAc; EtOAc phase was washed with water twice, saturated NaCl solution (once) and then dried over anhydrous sodium sulfate, filtered, concentrated; the residue was purified with silica column to give the desired title product (3.30 g) with recovered starting pyrrole (6.31 g). The title compound, ESI MS (m/z): 258 (M+H)+.

Provenance & Evidence