Diethyl Ether → 2-(4-nitrobenzoyl) pyrrole

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Reaction Steps

CH3MgBr (3M) in diethylether (30 mL, 90 mmol) was added by dropwise to the solution of pyrrole (6.95 mL, 100 mmol) in THF (150 mL) at −78° C. and continued for 1 h at r.t. 4-nitrobenzoyl chloride (13 g, 70 mmol) in THF (200 mL) was added by dropwise to the solution and stirring was continued for 3 hours at r.t. The mixture was poured into saturated aqueous NH4Cl, and the precipitate dissolved in DCM and added to the aqueous solution. The organic layer was washed with water, dried over MgSO4 and concentrated under vacuum to give an oily product. Compound 1 was isolated by chromatography on silica gel flash column eluting with EtOAc/Hex to furnish a yellow solid (12.4 g, 81%). 1H-NMR (CDCl3) δ 10.01 (bs, 1H, NH), 8.34 (d, J=8.4, 2H), 8.03 (d, J=8.7, 2H), 7.24 (bs, 1H), 6.86 (bs, 1H), 6.38 (bs, 1H); 13C-NMR (CDCl3) δ 182.51, 149.61, 143.62, 130.57, 129.74, 126.67, 123.55, 120.37, 111.69. ESI-MS m/z (M+H) calc'd: 217.0 found 216.9.

Provenance & Evidence