Triethyl phosphite → Diethyl 4-(trifluoromethyl)benzylphosphonate

HRID 1733816Notes

Reaction equation

HRID 1733816 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[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:10]=[CH:9][C:6]([CH2:7][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 15819199Diethyl 4-(trifluoromethyl)benzylphosphonateYield 89%

Procedure

A mixture of 4-trifluoromethylbenzyl bromide (5.68 g, 23.8 mmol) and triethyl phosphite (10.4 g, 63 mmol) was heated at reflux under nitrogen for 5 hours. The excess triethyl phosphite was removed by distillation and the crude product was purified by distillation at 95° C. (0.07 mm Hg.) to give 6.27 g, 89% of the product as an oil. D.C.I.M.S.[MH+, 297].

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 5 hours
  3. customThe excess triethyl phosphite was removed by distillation
  4. distillationthe crude product was purified by distillation at 95° C. (0.07 mm Hg.)

Sources & evidence

ORD record
ord-cb30d4fe0bbd4bd18850796cf6ea4f2b
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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