Hydrochloric Acid → HCID 86718776, compound

Temperature

4 °C

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).

1. additionAfter the addition
2. customThe resulting reaction mixture
3. stirringto stir at room temperature for 24 hours
4. concentrationthe resulting mixture was concentrated under reduced pressure
5. customto remove most of the acetonitrile
6. extractionThe aqueous mixture was extracted with ethyl acetate
7. washthe combined organic layer was washed with water
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto give a yellow solid
12. concentrationThe resulting mixture was concentrated
13. customto removed ethanol
14. customto give the product which
15. customwas crystallized from MTBE-EtOH

ORD record

ord-985e5f224f074dc49e5584371e4591c2

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296696B2