Carbon tetrabromide → HCID 67468969, Verbindung

HRID 1019759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019759
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:14][CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67469173HCID 67469173, Verbindung

Produkt 1

HCID 67468969HCID 67468969, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (7.0 g, 30.22 mmol), triphenylphosphine (12.68 g, 48.3 mmol) and carbon tetrabromide (14.03 g, 42.3 mmol) in DCM (150 mL) was stirred at room temperature for 2 hours. The mixture was partitioned between water (150 mL) and EtOAc (100 mL), and then the separated aqueous phase was extracted with EtOAc (100 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM to give the title compound (8.0 g, 90%) as a solid.

Aufarbeitung

  1. customThe mixture was partitioned between water (150 mL) and EtOAc (100 mL)
  2. extractionthe separated aqueous phase was extracted with EtOAc (100 mL)
  3. washThe combined organic extracts were washed with water (80 mL), brine (80 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-a69b0bc378644f0381fadba5a9476ad4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716287B2

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