Chloroacetyl chloride → 8-bromo-6-chloro-4H-benzo[1,4]oxazin-3-one

Reaction equation

[Br:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:12])[CH:3]=1.NC1C=C(Cl)C=C(Br)C=1[OH:22].ClCC(Cl)=O>>[Br:1][C:2]1[C:11]2[O:10][CH2:9][C:8](=[O:22])[NH:7][C:6]=2[CH:5]=[C:4]([Cl:12])[CH:3]=1

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 155210892-Amino-6-bromo-4-chlorophenol

HCID 225572348-Bromo-6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine

Product 1

HCID 142884678-bromo-6-chloro-4H-benzo[1,4]oxazin-3-one

Procedure

8-Bromo-6-chloro-2,3-dihydro-benzo[1,4]oxazine used in this Example was prepared by first reacting 2-amino-6-bromo-4-chloro-phenol with chloroacetyl chloride to provide 8-bromo-6-chloro-4H-benzo[1,4]oxazin-3-one using the procedure reported by Combs et al.; J. Med. Chem.; 33; 380-386 1990. This benzoxazinone was then reduced to 8-bromo-6-chloro-2,3-dihydro-benzo[1,4]oxazine using borane in THF according to the procedure described in Tetrahedron; 53(26); 8853-8870 1997.