Diethyl[(4-nitrophenyl)(difluoro)methyl]phosphonate → Diethyl[(4-aminophenyl)(difluoro)methyl]-phosphonate

HRID 511420Notes

Reaction equation

HRID 511420 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([F:12])[F:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([F:11])[F:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 10881410Diethyl[(4-nitrophenyl)(difluoro)methyl]phosphonate2×

Product 1

HCID 21088750Diethyl[(4-aminophenyl)(difluoro)methyl]-phosphonateYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Diethyl [(4-nitrophenyl)(difluoro)methyl]phosphonate (Compound 188B, 267 mg) was hydrogenated in the presence of 10% Pd/C (30 mg) in MeOH (10 mL) under 1 atmosphere for 4 h. The catalyst was filtered off, the filtrate was concentrated, and the residue was purified by silica gel chromatography (2% MeOH in DCM) to afford 201 mg of the desired product (yield: 83%). 1H NMR (CDCl3, 400 MHz): δ=1.35 (t, J=7.6 Hz, 6 H), 4.08 (s, br, 2 H), 4.31 (q, J=7.6 Hz, 4 H), 6.64 (d, J=8.8 Hz, 2 H), 7.86 (d, J=8.0 Hz, 2 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography (2% MeOH in DCM)

Sources & evidence

ORD record
ord-467a4463203646b2afc5a1ffc84b808c
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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