N-bromobutanimide → 4-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Participants

Reaction Steps

A mixture of 800 mg of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline and 90 mL of acetonitrile was treated with 510 mg of N-bromosuccinimide (NBS) at −20° C. for 2 minutes. The reaction was quenched with water and extracted with EtOAc three times. The organic layers were combined and washed with 10% aqueous sodium thiosulfate (Na2S2O3) solution, water, and brine and then dried over magnesium sulfate. The residue was purified by flash chromatography to yield 776 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline as a solid.

Provenance & Evidence