Chloroacetyl chloride → 5,8-Difluoro-4H-benzo[1,4]oxazin-3-one

HRID 1191488Notes

Reaction equation

HRID 1191488 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][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+]>>[F:8][C:7]1[C:2]2[NH:1][C:13](=[O:14])[CH2:12][O:10][C:3]=2[C:4]([F:9])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 151454932-Amino-3,6-difluorophenol

Product 1

HCID 689120095,8-Difluoro-4H-benzo[1,4]oxazin-3-oneYield 93.6%

Procedure

2-Amino-3,6-difluorophenol (0.44 g, 3.0 mmol), 2-chloroacetyl chloride (0.38 g, 3.3 mmol) and K2CO3 (0.88 g, 6.4 mmol) were mixed according to GP1. Purified by extraction gave the title compound (0.52 g, 93%). Rf=0.57 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) δ 8.02 (s, 1H), 7.78-6.69 (m, 2H), 4.72 (s, 2H); 13C NMR (CDCl3) δ 163.7, 148.0 (dd, J=242.4 Hz, J=2.1 Hz), 145.9 (d, J=237.9 Hz), 132.9 (dd, J=16.7 Hz, J=4.4 Hz), 117.2 (dd, J=16.9 Hz, J=3.8 Hz), 110.2 (dd, J=20.5 Hz, J=8.6 Hz), 108.6 (dd, J=20.0 Hz, J=7.7 Hz), 67.4.

Workup

  1. customPurified by extraction

Sources & evidence

ORD record
ord-c26e30d860f24b0185b31a2333f3be9d
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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