Iodine → Methyl 2-bromo-5-iodo-4-methylbenzoate

HRID 541308

Reaktionsgleichung

Reaktionsgleichung von HRID 541308
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:13]I.S(=O)(=O)(O)O>CC(O)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 21779704Methyl 2-bromo-4-methylbenzoate

Produkt 1

HCID 69844638Methyl 2-bromo-5-iodo-4-methylbenzoateAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a round-bottom flask was added a mixture of methyl 2-bromo-4-methylbenzoate (2.00 g, 7.86 mmol, 1.00 equiv) in AcOH (20 mL). I2 (2.45 g, 9.65 mmol, 1.10 equiv), NaIO4 (950 mg, 4.42 mmol, 0.50 equiv), and sulfuric acid (0.1 mL, 0.15 equiv) were added and the resulting mixture was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction was carefully quenched with Na2S2O3 (aq., sat.). The resulting mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to yield 2.50 g (81%) of the title compound as an off-white solid.

Aufarbeitung

  1. additionTo a round-bottom flask was added
  2. temperatureAfter cooling to ambient temperature
  3. customthe reaction was carefully quenched with Na2S2O3 (aq., sat.)
  4. extractionThe resulting mixture was extracted with 2×50 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e045711f0c8648bfb6adecd963342007
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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