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tert-butyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
66%
To a solution of <strong>[1073968-64-5]5-bromo-1,2,3,4-tetrahydroquinoline hydrochloride</strong> (0.90 g, 3.621 mmol) in dichloromethane (6 mL), N,N-dimethylaminopyridine (0.044 g, 0.362 mmol) and triethylamine (1.06 mL, 7.6 mmol) were added. The mixture was stirred for 30 min at room temperature, then di-tert-butyl dicarbonate (0.873 mL, 3.802 mmol) was added portionwise. The solution was stirred at room temperature overnight. The mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, filtered, and the filtrate was dried and concentrated. The mixture was purified by flash chromatography (SiO2, heptane-ethylacetate gradient). Pure fractions were combined and concentrated. The residue was dried under reduced pressure to yield tert-butyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate, cpd 127a (749 mg, 66% yield). MS m/z 213.9 (M+H-tBu)+.
Chemistry
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Material Science
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