Hydrochloric Acid → Methyl 4-(2-(3-bromophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

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Reaction Conditions

Reaction Steps

A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.295 g, 1.93 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.714 g, 5.35 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of 2-(3-bromophenyl)acetyl chloride (48) (0.500 g, 2.14 mmol) in anhydrous DCM (5 mL) was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2×50 mL). The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product, which was used directly in the next stage; m/z (LC-MS, ESI−), RT=2.46 min (M−H=350.00).

Provenance & Evidence