Phenol → 1-Bromo-2-nitro-4-phenoxymethyl-benzene

HRID 2358818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2358818
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 24809228(4-Bromo-3-nitrophenyl)methanol

Produkt 1

HCID 684618561-Bromo-2-nitro-4-phenoxymethyl-benzeneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product from Example 221a (0.5 g, 2.15 mmol) was combined with phenol (0.203 g, 2.15 mmol) and triphenylphosphine (0.735 g, 2.80 mmol) in anhydrous THF (7 mL) under nitrogen and the resulting solution cooled in an ice bath. To the cold solution was added dropwise diisopropylazodicarboxylate (0.467 mL, 2.37 mmol). Stirring at 0° C. was continued for 15 min then the cold bath was removed and the reaction mixture allowed to warm to room temperature and 90 min before quench and workup by pouring into dilute HCl and extraction with ether. The combined extracts were dried MgSO4, filtered and concentrated under vacuum giving the crude title compound that was purified by flash chromatography on silica gel eluting with EtOAc-hexanes to give the title compound (0.162 g, 25%).

Aufarbeitung

  1. temperaturethe resulting solution cooled in an ice bath
  2. customthe cold bath was removed
  3. temperatureto warm to room temperature and 90 min
  4. custombefore quench
  5. additionworkup by pouring into dilute HCl and extraction with ether
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude title compound that
  9. customwas purified by flash chromatography on silica gel eluting with EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4215599b574b4ed8941a58d77a5376fd
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763731B2

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