Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

HRID 1295583Notes

Reaction equation

HRID 1295583 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 13675396Diethyl 3-NitrobenzylphosphonateYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-nitrobenzyl bromide (17.3 g, 0.08 mol), triethyl phosphite (13.3 g, 0.08 mol) in toluene (200 mL) was stirred at reflux for 24 h. The reaction mixture was cooled and evaporated in vacuo. Chromatography of the residues on SiO2 eluting from 0–100% ethyl acetate in petroleum ether (60–80° C.) gave the title compound (14.8 g, 68%) as a yellow liquid.

Workup

  1. temperatureat reflux for 24 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-0889e9f234de4bcb8da5c6f93585c8f8
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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