반응 #2129016

반응 방정식

HCl

diethyl 3,4,5-trifluorophenylphosphonate

→

solvent

수율 76.0%

3,4,5-trifluorophenylphosphonic acid

수율 76.0%

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 12 hours
2. 2
   기타A brown oil was obtained
3. 3
   온도after cooling
4. 4
   기타removal of the solvent
5. 5
   workup.ADDITION12 mL of 8 M HCl was added
6. 6
   온도the reaction mixture refluxed again for several days
7. 7
   온도to cool
8. 8
   workup.WAITstand for several weeks
9. 9
   기타An off-white solid was obtained

실험 절차

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).

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