Imidazole → 1-Ethoxy-2-(2-iodoethyl)benzene

HRID 870468

Reaktionsgleichung

Reaktionsgleichung von HRID 870468
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11]O)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:37]I>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][I:37])[CH3:2]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 2512712-(2-Ethoxyphenyl)ethanol

Produkt 1

HCID 895575981-Ethoxy-2-(2-iodoethyl)benzeneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 50-mL round-bottom flask was placed dichloromethane (20 mL) and 2-(2-ethoxyphenyl)ethan-1-ol (1.33 g, 8.00 mmol, 1.00 equiv). The solution was cooled to 0° C. in a water/ice bath. Then PPh3 (2.72 g, 10.37 mmol, 1.30 equiv), imidazole (707 mg, 10.40 mmol, 1.30 equiv) and I2 (2.44 g, 9.61 mmol, 1.20 equiv) were added. The resulting solution was stirred at room temperature overnight. The reaction was then quenched by the addition of 50 mL of NaHSO3 (aq.). The organic layer was separated and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:100). Purification afforded 1.34 g (61%) of 1-ethoxy-2-(2-iodoethyl)benzene as a colorless oil.

Aufarbeitung

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 50 mL of NaHSO3 (aq.)
  3. customThe organic layer was separated
  4. concentrationconcentrated under vacuum
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-195563b2318b40aeb23418b499615596
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969557B2

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