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Triethyl phosphite → Diethyl {[3,5-bis(trifluoromethyl)phenyl]methyl}phosphonate

HRID 1733820
Notes
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Reaction equation

HRID 1733820 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6]Br.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1225733,5-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 15818097Diethyl {[3,5-bis(trifluoromethyl)phenyl]methyl}phosphonateYield 48%

Conditions

Temperature
160 °C

Procedure

A mixture of 3,5-bis-trifluoromethylbenzyl bromide (5.0 g, 16 mmol) and triethyl phosphite (3.4 g, 20 mmol) was heated at 160° C. for 20 hours. The reaction mixture was cooled and distilled at 83° C. (0.03 mm Hg) to give 2.36 g of the product as a colorless oil in 48% yield. D.C.I.M.S. [MH+, 365].

Workup

  1. temperature
The reaction mixture was cooled
  • distillationdistilled at 83° C. (0.03 mm Hg)
  • Sources & evidence

    ORD record
    ord-db4959e863844bc9b94bb67c37812c97
    Source dataset
    uspto-grants-1996_07
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05532226

    Reaction notes

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    On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes