Triethyl phosphite → Diethyl [(3,4-dichlorophenyl)methyl]phosphonate

HRID 1793638Notes

Reaction equation

HRID 1793638 reaction equation
C([O:3][P:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15]Br.P([O-])([O-])[O-]>>[CH2:9]([O:8][P:4]([CH2:15][C:14]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:12]([Cl:11])[CH:13]=1)(=[O:3])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

4

Reactant 3

HCID 31215Triethyl phosphite2×HCID 107908PhosphiteHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 116026Diethyl [(3,4-dichlorophenyl)methyl]phosphonate

Conditions

Temperature
80 °C

Procedure

Triethylphosphite (4.28 ml) was added dropwise to 3,4-dichlorobenzylbromide (6.0 g, 25 mmol) at rt with stirring. After 1 ml of triethylphosphite was added, the mixture was heated to 80° C. until an exothermic reaction was started. The remaining phosphite was added at a rate sufficient to maintain the reflux. After the addition was completed, the mixture was heated to reflux for 1 h and allowed to cool. The crude product was distilled under vacuum at 155–158° C./1–2 torr to afford (3,4-dichlorobenzyl)-phosphonic acid diethyl ester (6.5 g).

Workup

  1. temperatureto maintain the reflux
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 1 h
  5. temperatureto cool
  6. distillationThe crude product was distilled under vacuum at 155–158° C./1–2 torr

Sources & evidence

ORD record
ord-9206c04afd5e46ee8b918e129e7dcd7a
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

Loading…