N-bromobutanimide → HCID 121282944, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrol-2-yl)-2-cyclopropylethanone (Step 1)(0.30 g, 1.04 mmol) in THF (10 ml) at −78° C. was added a solution of N-bromosuccinimide (0.18 g, 1.04 mmol) in THF (10.0 ml) in a drop wise manner. The resulting mixture was stirred at −78° C. for 10 min. The progress of the reaction was monitored by TLC. The reaction mixture was quenched by the addition of a saturated sodium bicarbonate solution (5 ml). The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (30 ml). The organic layer was washed with a saturated sodium bicarbonate solution (1×10 ml) followed by water (1×10 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product which was purified by column chromatography using 10% ethyl acetate in hexanes to obtain the title compound 4(0.34 g, 89.0%). MS: m/z 367 (M+1).

Provenance & Evidence