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

HRID 1375232Notes

Reaction equation

HRID 1375232 reaction equation
[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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 86600743Dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-semicarbazonopropylphosphonate

Product 1

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

Procedure

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).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through short column of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98996995b7e94c0db7ef889a6f35b4f7
Source dataset
uspto-grants-2007_01
Patent number
US07166730B2

Reaction notes

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