Triethyl phosphite → Diethyl 4-nitrobenzylphosphonate

HRID 907370Notes

Reaction equation

HRID 907370 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([O:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18])[CH3:13]>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][P:15](=[O:19])([O:16][CH2:17][CH3:18])[O:14][CH2:12][CH3:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 660114-Nitrobenzyl bromide

Product 1

HCID 256065Diethyl 4-nitrobenzylphosphonateYield 964.2%

Conditions

Temperature
160 °C

Procedure

A mixture of 4-nitrobenzyl bromide (2.05 g, 0.949 mmol) and triethylphosphite (2.23 g, 1.34 mmol) was heated at 160° C. under a nitrogen atmosphere for 2 h. The excess triethylphosphite was removed in vacuo to give the sub-title compound as a brown oil (2.50 g, 96%).

Workup

  1. customThe excess triethylphosphite was removed in vacuo

Sources & evidence

ORD record
ord-25215e1356374678a74b5d0bb5882ac4
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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