Sodium Carbonate → N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17275

Reaktionsgleichung

Reaktionsgleichung von HRID 17275
[Br:1][C:2]1[C:7]([O:8]C)=[C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([C:17]#[N:18])=[C:4]([CH3:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.BrB(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:13])[CH3:14])[C:5]([C:17]#[N:18])=[C:4]([CH3:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 86630799N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

Produkt 1

HCID 86630803N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamideAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide (I-12) (630 mg, 1.41 mmol) was dissolved in dichloromethane (dewatered, 20 ml) under nitrogen atmosphere, cooled at −70° C. in a dry ice-methanol bath. 1 M tribromoborane (dichloromethane solution) (4.23 ml) was dropwise added to it at −70° C. to −68° C., followed by stirring for 2 hours with heating up to 0° C. The reaction liquid was diluted with cold water, followed by pH control at 6 to 7 by addition of aqueous 10% sodium carbonate solution. The organic matter was extracted with ethyl acetate, washed with saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2) to obtain the entitled compound (503 mg, 82%) as a pale yellow solid.

Aufarbeitung

  1. temperaturewith heating up to 0° C
  2. customThe reaction liquid
  3. extractionThe organic matter was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

Quellen und Nachweise

ORD-Eintrag
ord-b841381e700d49a1be971cf84131fb70
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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