3-Nitrobenzaldehyde → [Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl ester

HRID 1843599Notes

Reaction equation

HRID 1843599 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].C(N(CC)CC)C.[P:19]([O-:24])([O:22][CH3:23])[O:20][CH3:21]>C(OCC)(=O)C>[CH3:21][O:20][P:19]([CH:7]([OH:8])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:24])[O:22][CH3:23]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 8471TriethylamineHCID 21884954Dimethylphosphite

Product 1

HCID 11299958[Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-Nitrobenzaldehyde (20 g, 0.132 mol) was dissolved in 100 mL of ethyl acetate. Triethylamine (22 mL, 0.158 mol, 1.2 eq) was added, followed by dimethyl phosphite (15.7 mL, 0.171 mmol, 1.3 eq) and the mixture was stirred at room temperature. After 2 hours the mixture was diluted with 150 mL of ethyl acetate and washed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was treated with ethyl ether to obtain a beige solid, which was filtered and dried under vacuum at 40° C. for 1 h (26.7 g, 77% yield).

Workup

  1. washwashed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with ethyl ether
  5. customto obtain a beige solid, which
  6. filtrationwas filtered
  7. customdried under vacuum at 40° C. for 1 h (26.7 g, 77% yield)

Sources & evidence

ORD record
ord-66835638f2ce46caaf613184493eb821
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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