Potassium Carbonate → 4-(2-Nitro-4-phenoxymethyl-phenylsulfanyl)-phenol

HRID 2197984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197984
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[SH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:16]([C:3]1[CH:4]=[C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:2]=1[S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:18])=[O:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 684618561-Bromo-2-nitro-4-phenoxymethyl-benzene

Produkt 1

HCID 684589784-(2-Nitro-4-phenoxymethyl-phenylsulfanyl)-phenolAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product from Example 221b (0.16 g, 0.52 mmol) was reacted with 90% 4-mercapto-phenol (0.073 g, 0.52 mmol) in DMF at 80° C. under nitrogen in the presence of potassium carbonate (0.126 g, 0.91 mmol). The reaction was quenched after 18 h by pouring into dilute HCl and extraction with ether. The combined extracts were dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by flash chromatography on silica gel eluting with EtOAc-hexanes to give the title compound (0.155 g, 84%).

Aufarbeitung

  1. customThe reaction was quenched after 18 h
  2. additionby pouring into dilute HCl and extraction with ether
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. customThe crude product was purified by flash chromatography on silica gel eluting with EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-67855ede8354459096b4a05fca1fe66a
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338605B2

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