Triethyl phosphite → Diethyl (3-methoxy-4-nitrobenzyl)phosphonate

HRID 2279703Notes

Reaction equation

HRID 2279703 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1.[P:14]([O:21]CC)([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>>[CH3:13][O:12][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10])[CH2:2][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 220516194-(Chloromethyl)-2-methoxy-1-nitrobenzene2×

Product 1

HCID 86654016Diethyl (3-methoxy-4-nitrobenzyl)phosphonate

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(chloromethyl)-2-methoxy-1-nitrobenzene (Compound 1H, 1.1 g, 5.46 mmol) and triethyl phosphite (1.09 g, 6.55 mmol) were heated at 100° C. for 16 h in a sealed tube. The reaction mixture was concentrated under reduced pressure to yield a black oil. The crude material was purified by silica gel chromatography on a Teledyne ISCO CombiFlash® Rf system using DCM/MeOH (100:0→95:5) as eluent to afford the title compound as 1.08 g of an orange oil (65%). MS (ESI): m/z 304.0902 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto yield a black oil
  3. customThe crude material was purified by silica gel chromatography on a Teledyne ISCO CombiFlash® Rf system

Sources & evidence

ORD record
ord-42792984964d4604ac10436dc9a0ff5b
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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