Cyclohexylamine → 2-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

HRID 1604732

Reaction equation

HRID 1604732 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

HCID 867548802-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d69da30bdfc844c8b1ce6a7cf18b2ca6
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Linked notes

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