Chloroacetyl chloride → 6-bromo-8-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2103160Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].Cl[CH2:12][C:13](Cl)=[O:14].C([O-])([O-])=O.[K+].[K+]>>[Br:8][C:6]1[CH:5]=[C:4]([F:9])[C:3]2[O:10][CH2:12][C:13](=[O:14])[NH:1][C:2]=2[CH:7]=1

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 11430Potassium Carbonate

HCID 27376372-Amino-4-bromo-6-fluorophenol

Product 1

HCID 468564636-bromo-8-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 97.3%

Procedure

2-Amino-4-bromo-6-flourophenol (95MF2084) (0.078 g, 0.38 mmol), 2-chloroacetyl chloride (0.048 g, 0.42 mmol) and K2CO3 (0.11 g, 0.79 mmol) were mixed according to GP1 to give the title compound as a crude (95MF44) (0.091 g)

Sources & evidence

ORD record: ord-c2eb6c9af7954ae0ac53d1933cdec136
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576100B2

Reaction notes

Loading…