Cyclohexylamine → 2-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

HRID 1604732

Reaktionsgleichung

Reaktionsgleichung von HRID 1604732
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1C=O.C[Si]([O:17][P:18]([O:24][Si](C)(C)C)[O:19][Si](C)(C)C)(C)C.C1(N)CCCCC1.[O:36]1CCC[CH2:37]1>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[O:17][P:18]([CH2:37][OH:36])(=[O:24])[OH:19]

Komponenten

5

Edukt 4

HCID 7965CyclohexylamineHCID 8028TetrahydrofuranHCID 137213Tris(trimethylsilyl) phosphiteHCID 27347702-Fluoro-5-nitrobenzaldehyde

Produkt 1

HCID 867548802-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

Versuchsvorschrift

2-Fluoro-5-nitrobenzaldehyde (1.75 g, 10.0 mmol) was dissolved in tetrahydrofuran(50 mL). Tris(trimethylsilyl)phosphite (3.45 mL, 10.0 mmol) was added. The reaction mixture was stirred for 2.5 hours. Evaporation gave an oil which was dissolved in ethanol-ether. Addition of cyclohexylamine (1.14 mL,10.0 mmol) gave a solid salt which was filtered. Recrystallization from water gave 1.88 g (53.0%) of analytically pure product, mp 226-231° C.1H NMR (DMSO): d, 8.47 (m,1H), 8.11 (m,1H), 7.34 (t,1H), 4.85 (d,1H). MS (neg FAB): 249.9 (M-H). C7H7FNO6P/C6H13N.

Aufarbeitung

  1. customEvaporation
  2. customgave an oil which
  3. customgave a solid salt which
  4. filtrationwas filtered
  5. customRecrystallization from water
  6. customgave 1.88 g (53.0%) of analytically pure product, mp 226-231° C

Quellen und Nachweise

ORD-Eintrag
ord-d69da30bdfc844c8b1ce6a7cf18b2ca6
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994563

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