Ammonia → 2-(4-Iodophenyl)ethan-1-ol

HRID 735023

Reaktionsgleichung

Reaktionsgleichung von HRID 735023
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[I-:11].[Na+].NCCN.N>[Cu]I.O.O1CCOCC1>[I:11][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 3301EthylenediamineHCID 5238Sodium IodideHCID 728512-(4-Bromophenyl)ethanol

Produkt 1

HCID 30407702-(4-Iodophenyl)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.474 g (2.48 mmol) of copper (I) iodide, 5 g (24.86 mmol 2-(4-bromophenyl)ethanol and 7.45 g (49.73 mmol) of sodium iodide are successively added to a flask under an argon atmosphere. Then 0.438 g (4.97 mmol) of dimethylenediamine and 25 mL dioxane are added and the reaction mixture is refluxed for 14 hours. Then the reaction mixture is combined with 20 mL concentrated ammonia solution at ambient temperature, with 100 mL of water diluted and extracted with dichloromethane. The organic phase is extracted three times with water and dried over sodium sulfate. Yield: 5.4 g (87.5% of theory); C8H9IO (M=248.06); calc.: molecular ion peak (M)+: 248; found: molecular ion peak (M)+: 248; Rf value: 0.6 (silica gel, dichloromethane/ethanol (10:1)).

Aufarbeitung

  1. temperaturethe reaction mixture is refluxed for 14 hours
  2. additiondiluted
  3. extractionextracted with dichloromethane
  4. extractionThe organic phase is extracted three times with water
  5. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-ba01858f6ae24ea0847813801ff18e2e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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