Allyl Alcohol → 3-(4-Bromo-2-methylphenyl)propanal

HRID 734834

Reaktionsgleichung

Reaktionsgleichung von HRID 734834
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([OH:13])[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][CH2:11][CH:10]=[O:13])=[C:4]([CH3:9])[CH:3]=1

Komponenten

8

Edukt 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 27246015-Bromo-2-iodotoluene

Produkt 1

HCID 822879023-(4-Bromo-2-methylphenyl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 1.00 g (3.39 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.58 g (10.00 mmol) of allyl alcohol, 0.69 g (8.20 mmol) of sodium bicarbonate, 0.92 g (3.30 mmol) of tetrabutylammonium chloride, and 22 mg (0.10 mmol) of palladium (II) acetate in 5 mL of DMF were stirred for 16 hours at 45° C. under argon. The reaction mixture was diluted with EtOAc, and the organic phase was washed with water, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/EtOAc 4:1). Yield: 0.60 (78% of theoretical); C10H11BrO (M=227.098); calc.: molpeak (M+H)+: 226/228 (Br); found: molpeak (M+H)+: 226/228 (Br); Rf value: 0.45 (silica gel, PE/EtOAc 4:1).

Aufarbeitung

  1. washthe organic phase was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated down in vacuo
  4. customThe residue was purified by column chromatography (silica gel, PE/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-40fa67226683452dbd5c8ffd0ab090eb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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