Iodine → 2-Iodo-4-methylaniline

HRID 532202

Reaktionsgleichung

Reaktionsgleichung von HRID 532202
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[I:14]I.OS([O-])=O.[Na+]>C(Cl)Cl.O>[I:14][C:4]1[CH:3]=[C:2]([CH3:1])[CH:8]=[CH:7][C:5]=1[NH2:6]

Komponenten

7

Edukt 4

HCID 807IodineHCID 7813p-ToluidineHCID 516892Sodium BicarbonateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 27640002-Iodo-4-methylanilineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methylaniline (53.5 g, 500 mmol) in DCM (200 mL) was added a solution of NaHCO3 (50.4 g) in water (500 mL), and then I2(127 g) was added. The mixture was stirred at rt overnight. The mixture was treated with aqueous NaHSO3 and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and then concentrated in vacuo to afford the product as brown oil (110 g, yield 95%). 1H NMR (300 MHz, CDCl3): δ 7.48 (dd, J=1.8 & 0.6 Hz, 1H), 6.96 (dd, J=8.1 & 1.8 Hz, 1H), 6.67 (d, J=8.1 Hz, 1H), 3.98 (bs, 2H), 2.22 (s, 3H) ppm.

Aufarbeitung

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36546288e7d84413b7c8915bda0764ca
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853186B2

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