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

HRID 1463573Notes

Reaction equation

HRID 1463573 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]

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. temperatureThe reaction mixture was cooled
  2. distillationdistilled at 83° C. (0.03 mm Hg)

Sources & evidence

ORD record
ord-6417252ce6454c0581d427adf64e2475
Source dataset
uspto-grants-1994_04
Patent number
US05300687

Reaction notes

Loading…