Carbon tetrabromide → HCID 67468969, Verbindung

HRID 1019745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019745
[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 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (0.85 g, 3.67 mmol) in DCM (20 mL), triphenylphosphine (1.54 g, 5.9 mmol) and carbon tetrabromide (1.46 g, 4.4 mmol) were added. The reaction mixture was maintained for 7 hours at room temperature then partitioned between water (50 mL) and EtOAc (80 mL). The separated aqueous phase was extracted with EtOAc (80 mL), then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane to give the title compound (0.9 g, 83%) as a solid.

Aufarbeitung

  1. customthen partitioned between water (50 mL) and EtOAc (80 mL)
  2. extractionThe separated aqueous phase was extracted with EtOAc (80 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-d0c6058e8f034612b58bc041950cde22
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716287B2

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