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

HRID 1191332Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].Cl[CH2:11][C:12](Cl)=[O:13].C([O-])([O-])=O.[K+].[K+]>>[F:8][C:4]1[C:3]2[O:9][CH2:11][C:12](=[O:13])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 11430Potassium Carbonate

HCID 6435622-Amino-6-fluorophenol

Product 1

HCID 552774648-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 86.8%

Procedure

2-Amino-6-fluorophenol (95MF2085) (0.256 g, 2.0 mmol), 2-chloroacetyl chloride (0.25 g, 2.2 mmol) and K2CO3 (0.583 g, 4.2 mmol) were mixed according to GP1 to give the title compound as a crude (95MF45) (0.29 g)

Sources & evidence

ORD record: ord-a2c0c1dda0404ba6acbb3a7f73fc8562
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680115B2

Reaction notes

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