Triethyl phosphite → Phosphonic acid, [(3-cyanophenyl)methyl]-, diethyl ester

HRID 2080130

Reaction equation

HRID 2080130 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br)#[N:2].[CH2:11]([O:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17])[CH3:12]>>[CH2:11]([O:13][P:14]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=1)(=[O:18])[O:15][CH2:16][CH3:17])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 21466817Phosphonic acid, [(3-cyanophenyl)methyl]-, diethyl esterYield 79.1%

Procedure

3-Cyanobenzyl bromide (9.8 g, 50 mmol) and triethylphosphite (9.97 g, 60 mmol) were stirred at 140° C. for 3 hours. The resulting residue was evaporated, the distillate which has 145° C./1 mmHg was collected, and the title compound (10 g, 39.5 mmol, 79.1%) was obtained as a colorless oil.

Workup

  1. customThe resulting residue was evaporated
  2. customhas 145° C.
  3. customwas collected

Sources & evidence

ORD record
ord-479d8d2d8a2a4504b2c621d45d245b55
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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