Benzyl Bromide → Methyl 1-benzyl-3-methyl-pyrrole-2-carboxylate

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Reaction Steps

To an ice/water-bath cooled solution of 3-methyl-1H-pyrrole-2-carboxylic acid methyl ester (1.196 g, prepared according to the literature: W. G. Terry, G. W. Kenner, and G. Kornis J. Chem. Soc. 1965, 4389-4393) and benzyl bromide (1.15 mL) in N,N-dimethylformamide (17 mL) was carefully added NaH (413 mg, 60% purity in mineral oil) under nitrogen. The mixture was stirred in the ice bath for 25 min and then quenched saturated ammonium chloride solution (5 mL). It was extracted with EtOAc, and the organic phase was washed with water and saturated NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated. The crude residue was column-purified to give the title compound (1.536 g) as white solid. 1H NMR (200 MHz, CDCl3) δ=7.32-6.98 (m, 5H), 6.75 (d, 1H, J=2.5 Hz), 6.02 (d, 1H, J=2.5 Hz), 5.48 (s, 2H), 3.75 (s, 3H), 2.33 (s, 3H).

Provenance & Evidence