tert-Butyl acrylate → 3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester

HRID 1515025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515025
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH:11]=[CH2:12].C([O-])(=O)C.[K+]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:15]([O:14][C:10](=[O:13])[CH:11]=[CH:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

7

Edukt 3

HCID 15458tert-Butyl acrylateHCID 764241,3-Dichloro-5-iodobenzeneHCID 517044Potassium Acetate

Produkt 1

HCID 536582813-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 16212273Tetrabutylammonium chloride hydrateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dichloro-iodobenzene (5 g, 18 mmol), tert butyl acrylate (6.5 mL, 2.5 eq), tetrabutyl ammonium chloride hydrate (5.1 g, 1 eq), potassium acetate (5.4 g, 3 eq) and palladium (II) acetate (˜200 mg, 30 mol %) in DMF (50 mL) was stirred at ambient temperature for 5 h. The reaction mixture was reduced in vacuo and partitioned between water and ethyl acetate. The ethyl acetate fractions were dried over magnesium sulphate and filtered through a small plug of silica gel using 10% ethyl aceate/n-heptanes as eluent to afford 3-(3,5-dichlorophenyl)-acrylic acid tert butyl ester as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ 7.81 (d, J=1.77 Hz, 2H), 7.59 (t, J=1.89 Hz, 1H), 7.49 (d, J=16.04 Hz, 1H), 6.69 (d, J=16.04 Hz, 1H), 1.46 (s, 9H).

Aufarbeitung

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe ethyl acetate fractions were dried over magnesium sulphate
  3. filtrationfiltered through a small plug of silica gel using 10% ethyl aceate/n-heptanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2093b45668d1459399c46fc32f1fd84c
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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