Chloroacetyl chloride → 5,6-Difluoro-4H-benzo[1,4]oxazin-3-one

HRID 1191486Notes

Reaction equation

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

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 11430Potassium Carbonate

HCID 184572512-Amino-3,4-difluorophenol

Product 1

HCID 689101445,6-Difluoro-4H-benzo[1,4]oxazin-3-oneYield 14.6%

Procedure

A crude of 2-amino-3,4-difluorophenol (0.68 g, 4.7 mmol), 2-chloroacetyl chloride (0.58 g, 5.2 mmol) and K2CO3 (1.36 g, 9.9 mmol) were mixed according to GP1. Purified by prep RP-HPLC to give the title compound (0.127 g, 14.5%). Rf=0.63 (heptanes/EtOAc 1:1). 1H NMR (CDCl3) δ 6.69-6.57 (m, 2H), 4.47 (s, 2H); 13C NMR (CDCl3) δ 165.0, 146.2 (dd, J=241.8 Hz, J=10.4 Hz), 140.3 (t, J=2.32 Hz), 138.7 (dd, J=247.2 Hz, J=17.3 Hz), 67.1 (t, J=2.7 Hz).

Workup

customPurified by prep RP-HPLC

Sources & evidence

ORD record: ord-09646e19cd4b41fc978ba49b9ebc5f99
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680115B2

Reaction notes

Loading…