3-Nitrobenzaldehyde → Diethyl P-[hydroxy(3-nitrophenyl)methyl]phosphonate

HRID 1265950Notes

Reaction equation

HRID 1265950 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[P:12]([O-:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].[F-].[K+]>C(Cl)Cl>[OH:8][CH:7]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 522689Potassium FluorideHCID 3780918Diethylphosphite

Product 1

HCID 97811Diethyl P-[hydroxy(3-nitrophenyl)methyl]phosphonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Nitrobenzaldehyde (4.53 g, 30 mmol) was dissolved in diethyl phosphite (4.14 g, 30 mmol) under gentle heating. The solution was brought to room temperature and KF (8.7 g, 0.15 mole) was added with rapid stirring. After 30 min the mixture was suspended in CH2Cl2 (150 ml). The resultant suspension was filtered and the filtrate was concentrated under reduced pressure furnishing 8.57 g (99%) of 17 as a yellow colored solid, mp 93-95° C., IR (neat): 3750-3040, 1540, 1355, 1205 and 1050; 1H NMR (200 MHz, CDCl3): δ1.23 (6H, m), 4.10 (4H, m), 5.14 (1H, d, J=12 Hz), 5.94 (1H, s, OH) and 7.93 (4H, m); 13C NMR (50 MHz, CDCl3): δ17.6, 64.2, 64.9, 72.1, 122.4, 123.1, 129.3, 133.4, 139.8 and 148.3; HR-MS (EI): m/e 289.0715 (M+C11H16NO6P requires 289.0714).

Workup

  1. customwas brought to room temperature
  2. filtrationThe resultant suspension was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-47269ccb1e2a4d2a8c6d779d443f1e92
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

Loading…