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

HRID 2354113Notes

Reaction equation

HRID 2354113 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-e5eb978ec21542fd91da472ca3adea93
Source dataset
uspto-grants-2010_07
Patent number
US07750167B2

Reaction notes

Loading…