Triethyl phosphite → Diethyl 3-trifluoromethylbenzylphosphonate

HRID 1733810Notes

Reaction equation

HRID 1733810 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzene

Product 1

HCID 11162251Diethyl 3-trifluoromethylbenzylphosphonate

Procedure

A mixture of 3-trifluoromethylbenzyl bromide (5.74 g, 24.0 mmol) and triethyl phosphite (4.98 g, 30 mmol) was heated at reflux under nitrogen for 3 hours. The excess triethyl phosphite was removed by distillation and the crude product obtained was distilled at 140°-145° C. at 4 mm to yield 6.44 g (90.7%) of analytically pure product as a clear liquid. 300 MHz 1H NMR (CDCl3): δ, 3.20 (d,2H J=21.78 Hz, PCH2). D.C.I.M.S.[MH+, 297].

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. customThe excess triethyl phosphite was removed by distillation
  4. customthe crude product obtained
  5. distillationwas distilled at 140°-145° C. at 4 mm
  6. customto yield 6.44 g (90.7%) of analytically pure product as a clear liquid

Sources & evidence

ORD record
ord-dbf29fa35ef34f1bb03e33e90e501c06
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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