Hydrochloric Acid → 1160299-57-9

HRID 84983Notes

Reaction equation

HRID 84983 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([P:11](=[O:18])([O:15]CC)[O:12]CC)[CH:6]=[C:7]([F:10])[C:8]=1[F:9]>>[F:2][C:3]1[CH:4]=[C:5]([P:11](=[O:12])([OH:18])[OH:15])[CH:6]=[C:7]([F:10])[C:8]=1[F:9]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86653410Diethyl (3,4,5-trifluorophenyl)phosphonate

Product 1

HCID 582622131160299-57-9Yield 76%

Procedure

12 M HCl (12 mL, excess) was added to diethyl 3,4,5-trifluorophenylphosphonate (320 mg) in a round bottom flask. The reaction mixture was refluxed for 12 hours. A brown oil was obtained after cooling and removal of the solvent. 1H NMR showed the presence of unreacted starting material. 12 mL of 8 M HCl was added and the reaction mixture refluxed again for several days. The mixture was allowed to cool and stand for several weeks. An off-white solid was obtained after removal of the solvent (190 mg, 76% yield). 1H NMR (400.14 MHz, DMSO) δ 7.49-7.42 (m, 2H). 13C {1H} NMR (100.62 MHz, DMSO) δ 150.1 (dddd, J=251.0, 23.7, 7.3, 2.6 Hz, 2C), 140.5 (dtd, J=253.1, 15.3, 2.6 Hz), 131.8 (dm, J=178.4 Hz), 115.3-114.9 (m, 2C). 31P {1H} NMR (161.97 MHz, DMSO): δ 9.22. Analysis calculated (found) %: C 33.98 (33.94), H 1.90 (1.80). MS (FAB, m/z): 213 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 212.99284 (212.99418).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. customA brown oil was obtained
  3. temperatureafter cooling
  4. customremoval of the solvent
  5. addition12 mL of 8 M HCl was added
  6. temperaturethe reaction mixture refluxed again for several days
  7. temperatureto cool
  8. waitstand for several weeks
  9. customAn off-white solid was obtained

Sources & evidence

ORD record
ord-f1ff9d299c69442db405f363a6b6f22e
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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