2,2'-Bipyridine → Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoate

HRID 385101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385101
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13](I)[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1C1C=CC=CN=1.[CH3:29][S:30]SC>CN(C)C=O.[Zn].[Ni](Br)Br>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([S:30][CH3:29])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 14742,2'-BipyridineHCID 12232Dimethyl DisulfideHCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

Produkt 1

HCID 86668170Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoateAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 278492Nickel(II) bromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate (1.00 g) was dissolved in N,N-dimethylformamide (10 mL), and 2,2′-bipyridine (47 mg), zinc powder (391 mg), nickel bromide (66 mg) and dimethyl disulfide (142 mg) were added to the solution, and then the mixture was stirred at 130° C. for 1 hour. After the reaction solution was filtered, 1N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=12:1) to obtain the title compound (382 mg) as a pale yellow oily substance.

Aufarbeitung

  1. filtrationAfter the reaction solution was filtered
  2. addition1N hydrochloric acid was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=12:1)

Quellen und Nachweise

ORD-Eintrag
ord-0130ce09b54c4c719501736648c1348e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367843B2

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