Triethyl phosphite → Diethyl (4-Cyanobenzyl)phosphonate

HRID 1663235Notes

Reaction equation

HRID 1663235 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[P:11]([O:18]CC)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[CH2:13]([O:12][P:11]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:18])[O:15][CH2:16][CH3:17])[CH3:14]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 241438Diethyl (4-Cyanobenzyl)phosphonateYield 97%

Procedure

A mixture of 4-cyano-benzyl bromide (41.8 g, 0.213 mol) and triethyl phosphite (42 mL, 0.244 mol) was stirred in a flask equipped with a Dean-Stark trap at 150° C. for 6 h, then the reaction mixture was submitted to distillation in vacuo to yield 52.2 g (97%) of the title compound.

Workup

  1. customequipped with a Dean-Stark trap at 150° C. for 6 h
  2. distillationthe reaction mixture was submitted to distillation in vacuo

Sources & evidence

ORD record
ord-ffaf4e3d146d4dc8839ee9a51a75c33c
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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