Iodine → 2-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

HRID 1445758

Reaktionsgleichung

Reaktionsgleichung von HRID 1445758
[I:1]I.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16]O)[N:14]=2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16][I:1])[N:14]=2)=[CH:6][CH:5]=1

Komponenten

8

Edukt 4

HCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

Produkt 1

HCID 589513942-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add iodine (1.90 g, 7.49 mmol) to a stirred mixture of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.503 g, 5.33 mmol), triphenylphosphine (2.101 g, 8.01 mmol), and pyridine (1.4 mL, 17 mmol) in toluene (48 mL) and heat at 100° C. for 45 min. Cool to room temperature, add ethyl acetate and water, and separate the layers. Extract the aqueous layer twice with ethyl acetate, wash the organic layer with 0.1N HCl, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 3.49 (dd, J=7.2, 7.2 Hz, 2H), 3.11 (dd, J=7.2, 7.2 Hz, 2H), 2.39 (s, 3H).

Aufarbeitung

  1. temperatureCool to room temperature
  2. customseparate the layers
  3. extractionExtract the aqueous layer twice with ethyl acetate
  4. washwash the organic layer with 0.1N HCl
  5. dry with materialdry over anhydrous magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue
  8. washby flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-ceb9f050bd8e44138dbb19c5551d1f16
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

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