Hydrochloric Acid → HCID 86718776, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(tert-butyl)-8-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine (9.420 g, 77.09 mmol) in acetonitrile (100 mL) was added dropwise bromine (1.8 mL, 1.0 equiv) at 5-10° C. After the addition, the mixture was stirred at 3-5° C. for 130 min. The resulting reaction mixture was allowed to stir at room temperature for 24 hours. To the reaction mixture was added water (200 mL) and the resulting mixture was concentrated under reduced pressure to remove most of the acetonitrile. The aqueous mixture was extracted with ethyl acetate and the combined organic layer was washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure to give a yellow solid. The solid was dissolved in ethanol and treated with 37% HCl (3.65 g). The resulting mixture was concentrated to removed ethanol to give the product which was crystallized from MTBE-EtOH to give 6-bromo-3-(tert-butyl)-8-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine (3.118 g).

Provenance & Evidence