Ethyl Acetate → HCID 131730654, compound

Participants

Reaction Steps

To a 500 mL flask was added 400 mL dichloromethane and 31.5 g 8-(t-butyl)dimethylsiloxyquinaldine. The mixture was vigorously stirred while 33.14 g bromine (Aldrich) dissolved in 20 mL dichloromethane was added dropwise. The reaction progress was monitored by TLC (5:95 ethylacetate:hexanes). The starting material was found to be completely consumed. Excess bromine was removed by addition of 200 mL of saturated sodium thiosulfate (Aldrich). The organic layer was separated, washed with 150 ml water, 150 ml brine and then dried over MgSO4. After filtering off the salts, the filtrate was concentrated to an oil which was purified by column chromatography, eluting with 20% dichloromethane/hexanes to give 26.04 g of 5-bromo-8-(t-butyl)dimethylsiloxyquinaldine (compound 2ii) as a yellow oil.

Provenance & Evidence