Benzyl Bromide → Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylate

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Reaction Steps

To a stirred solution of 4 (0.72 g, 2.6 mmol) in acetone (20 mL) was added K2CO3 (0.71 g, 5.1 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Benzyl bromide (0.46 mL, 3.8 mmol) was added dropwise to the reaction mixture and the mixture was then refluxed for 16 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between ethyl acetate and water. The combined organic layer was dried over anhydrous MgSO4, filtered and then concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 5 as a white solid (0.85 g, 90%). 1H NMR (400 MHz, CDCl3) δ 9.66 (s, 1H), 7.50 (s, 1H), 7.24-7.25 (m, 3H), 6.98 (d, J=7.6 Hz, 2H), 5.75 (s, 2H), and 3.72 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 186.98, 160.33, 136.43, 128.97, 128.22, 127.84, 127.10, 126.59, 119.32, 92.81, 52.81, and 52.11.

Provenance & Evidence