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

HRID 1947991Notes

Reaction equation

HRID 1947991 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

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, 6H), 4.08 (s, br, 2), 4.31 (q, J=7.6 Hz, 4H), 6.64 (d, J=8.8 Hz, 2H), 7.86 (d, J=8.0 Hz, 2H).

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-d9eb83718a584a1092ab65b277eb9cfd
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…