Hydrochloric Acid → Dimethyl {2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl}phosphonate

Reaktionsgleichung

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][C:8](=NNC(N)=O)[CH2:9][P:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12].C(Cl)Cl.Cl.[OH2:30]>>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][C:8](=[O:30])[CH2:9][P:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12]

Komponenten

Edukt 4

HCID 313Hydrochloric Acid

HCID 962Water

HCID 6344Dichloromethane

HCID 86600743Dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-semicarbazonopropylphosphonate

Produkt 1

HCID 15003092Dimethyl {2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl}phosphonateAusbeute 93 %

Versuchsvorschrift

A mixture of dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-semicarbazonopropylphosphonate (19.2 g, 50 mmol), CH2Cl2 (50 mL) and 6 N HCl (50 mL) was stirred for 2 h at rt. Water (50 mL) was added to the mixture. The organic layer was separated, washed with brine, dried over Na2SO4, filtered through short column of silica gel and concentrated in vacuo to give 15.1 g (93%) of dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-oxopropylphosphonate as light yellow oil. 1H NMR (CDCl3) δ: 7.42 (t, J=8.0 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.11 (s, 1H), 7.07 (d, J=8.0 Hz, 1H), 4.77 (s, 2H), 3.80 (s, 3H), 3.74 (s, 3H), 3.23 (d, J=12 Hz, 2H).