Triethyl phosphite → Diethyl [(2-iodophenyl)methyl]phosphonate

HRID 1516873Notes

Reaction equation

HRID 1516873 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[I:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl>C1(C)C(C)=CC=CC=1>[CH2:9]([O:8][P:1]([CH2:14][C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=1[I:11])(=[O:2])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 1010641-(Chloromethyl)-2-iodobenzene

Product 1

HCID 15166404Diethyl [(2-iodophenyl)methyl]phosphonate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Triethyl phosphite (ca 66.6 ml; 94% pure; ca. 396.8 mmol) and 2-iodobenzyl chloride 1 (100 g, 400 mmol; melted prior to use) were mixed with xylene (65 ml) in a 250 ml roundbottomed flask. The clear solution was heated to reflux while stirring for 24 hours. The reaction was followed by GC and 1H-NMR (CDCl3). The disappearing proton resonance of 2H, s, CH2I at 4.73 ppm and the new 2H, d, CH2PO(OEt)2 at 3.47 ppm were indicative for the progress of the reaction.

Workup

  1. temperatureThe clear solution was heated
  2. temperatureto reflux
  3. customCH2PO(OEt)2 at 3.47 ppm were indicative for the progress of the reaction

Sources & evidence

ORD record
ord-a36a48e2ff8f47c0a8bc18738a56eba3
Source dataset
uspto-grants-2012_07
Patent number
US08227623B2

Reaction notes

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