Cesium fluoride → 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol

HRID 1919758Notes

Reaction equation

HRID 1919758 reaction equation
[F-].[Cs+].[CH:3](/B(O)O)=[CH:4]/[CH3:5].[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](I)[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](/[CH:3]=[CH:4]\[CH3:5])[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 59234900HCID 59234900, compound

Product 1

HCID 592350754-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenolYield 181.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

Cesium fluoride (1.24 g), cis-propenylboronic acid (1.54 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.49 g) were added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-iodo-6-propylphenol (2.83 g, 5.99 mmol) in toluene (60 mL) in an argon atmosphere at room temperature, followed by stirring overnight. After completion of the reaction, the reaction solution was extracted with ethyl acetate-water, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 4.20 g of the title compound (yield: 85%) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate-water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-777abd5c36164d63940b4d099d1284f3
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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