Hydrochloric Acid → 2-Iodonaphthalene

HRID 1096733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096733
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[I-:12].[K+].Cl>[Cu](I)I.CN(C)P(N(C)C)(N(C)C)=O>[I:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 113722-Bromonaphthalene

Produkt 1

HCID 1364122-IodonaphthaleneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

2-Bromonapthalene (50.0 g, 242.0 mmol), copper iodide (230.0 g, 1210.0 mmol, 5 eq.), potassium iodide (200 g, 1210.0 mmol, 5 eq.) and hexamethylphosphoramide (500 mL) were stirred and heated to 160° C. for 8 h. This was cooled and added to 1N HCl (250 mL) then toluene (300 mL) and ether (300 mL) and the mixture filtered through celite. The organic layer was separated and washed with water (2×250 mL) dried over magnesium sulphate and concentrated to afford 2-iodonaphthalene (61.5 g, 59%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.46-7.52 (2H, m, ArH, 7.55-7.58 (1H, m, ArH), 7.68-7.74 (2H, m, ArH), 7.76-7.82 (1H, m, ArH), 8.22-8.26 (1H, m, ArH).

Aufarbeitung

  1. temperatureThis was cooled
  2. filtrationtoluene (300 mL) and ether (300 mL) and the mixture filtered through celite
  3. customThe organic layer was separated
  4. washwashed with water (2×250 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-535ab3a6094f4779853b3af878ec9dfa
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138377B2

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