Diethyl methylphosphonite → HCID 178476798, compound

HRID 511228Notes

Reaction equation

HRID 511228 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.[CH3:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18]>>[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][CH2:14][PH:15](=[O:19])[O:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 85063Diethyl methylphosphoniteHCID 220516194-(Chloromethyl)-2-methoxy-1-nitrobenzene

Product 1

HCID 178476798HCID 178476798, compoundYield 195.5%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(chloromethyl)-2-methoxy-1-nitrobenzene (1.1 g, 5.46 mmol) and diethyl methylphosphonite (0.89 g, 1.2 mmol) were heated at 100° C. for 16 h in a sealed tube. The reaction mixture was concentrated in vacuo and the residue crude purified using an Isco Combiflash system eluting with 0→5% MeOH in DCM as eluent to afford 0.641 g of ethyl (3-methoxy-4-nitrobenzyl)methylphosphinate (yield: 43% yield). MS (ES+): m/z 273.99 [MH+] (ZQ3, polar 5 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue crude purified
  3. washeluting with 0→5% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-f29d0b5714f947ee82491a5597a1e6b6
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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