3-Chloro-4-methylaniline → 5-Chloro-2-iodo-4-methylaniline

HRID 272694

Reaktionsgleichung

Reaktionsgleichung von HRID 272694
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[I:10](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2]>C(Cl)Cl.CO.CCOCC>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:6]([I:10])=[C:4]([CH:3]=1)[NH2:5]

Komponenten

7

Edukt 3

HCID 72553-Chloro-4-methylanilineHCID 10112Calcium CarbonateHCID 56924451Trimethylbenzylammonium Dichloroiodate

Produkt 1

HCID 584754055-Chloro-2-iodo-4-methylanilineAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chloro-4-methylaniline (1.50 g, 10.6 mmol) and benzyltrimethylammonium dichloroiodate (4.60 g, 13.2 mmol) were dissolved in CH2Cl2 (50 mL) and MeOH (20 mL), then CaCO3 (3.10 g, 31.0 mmol) was added and the reaction stirred at room temperature overnight. The reaction was diluted with Et2O (200 mL), filtered through Celite®, and concentrated. The crude material was purified by column chromatography using 97.5/2.5 hexane/EtOAc, giving the product (1.80 g, 63%) as light tan solids. MS (DCI) m/e 268 and 270 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.48 (s, 1H), 6.76 (s, 1H), 4.00 (v br s, 2H), 2.22 (s, 3H).

Aufarbeitung

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4717a9b5d6464228960f5169b18f2799
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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