Trimethyl phosphite → Dimethyl [3,3-bis(4-fluorophenyl)-2-difluoromethyl-2-propen-1-yl]phosphonate

HRID 1086097Notes

Reaction equation

HRID 1086097 reaction equation
Br[CH2:2][C:3]([CH:19]([F:21])[F:20])=[C:4]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[CH3:22][O:23][P:24]([O:27]C)[O:25][CH3:26]>>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:3]([CH:19]([F:21])[F:20])[CH2:2][P:24](=[O:27])([O:25][CH3:26])[O:23][CH3:22])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 200593762-Bromomethyl-3,3-difluoro-1,1-bis(4-fluorophenyl)propene

Product 1

HCID 54009116Dimethyl [3,3-bis(4-fluorophenyl)-2-difluoromethyl-2-propen-1-yl]phosphonateYield 73.6%

Procedure

A solution of 2-bromomethyl-3,3-difluoro-1,1-bis(4-fluorophenyl)propene (0.5 g, 1.4 mmol) and trimethylphosphite (0.5 g, 4 mmol) was heated at relfux for 20 minutes. Excess trimethyl phosphite was removed in vacuo and the residue purified by chromatography on silica eluting with 40% ethyl acetate to give 0.4 g of the title compound as a viscous oil. MS(EI): m/e =388 for M+ of C18H17F4O3P.

Workup

  1. customExcess trimethyl phosphite was removed in vacuo
  2. customthe residue purified by chromatography on silica eluting with 40% ethyl acetate

Sources & evidence

ORD record
ord-9a7eb591956a47cb96398f7a0c069abc
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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