4-Fluoro-3-phenoxyphenylallylbenzene → Silafluofen

HRID 1197199

Reaction equation

HRID 1197199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[CH:10]C2C=CC=CC=2)=[CH:4][C:3]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([SiH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[CH3:25]>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH2:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([Si:33]([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:4]=2)([CH3:34])[CH3:35])=[CH:29][CH:28]=1)[CH3:25]

Participants

5

Reactant 2

HCID 678999714-Fluoro-3-phenoxyphenylallylbenzeneHCID 713607484-Ethoxyphenyldimethylsilane

Product 1

HCID 92430SilafluofenYield 81.4%

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 3776IsopropanolSolvent

Procedure

A few drops of a 30% solution of hexachloroplatinic acid in isopropanol are added twice at 22° C. to a mixture of 2.98 mol of 4-fluoro-3-phenoxyphenylallylbenzene (98.9% pure, 687 g) and 3.24 mol of 4-ethoxyphenyl(dimethyl)silane (595 g, 97.9% pure). After an induction phase of 11/2 hours, spontaneous heating to 130° C. takes place. After stirring is continued for a short period, 259 g of forerun are distilled off in a high vacuum of 0.4-0.15 mbar, followed by 1003 g of product (98.7% pure by GC). This corresponds to a yield of 81.4% of theory.

Workup

  1. waitis continued for a short period
  2. distillation259 g of forerun are distilled off in a high vacuum of 0.4-0.15 mbar

Sources & evidence

ORD record
ord-0bb0f255e5b14c86ba78804e6267fefc
Source dataset
uspto-grants-1992_05
Patent number
US05117028

Linked notes

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