Reaktion #628490

Reaktionsgleichung

methyl 2-bromo-4-methylbenzoate

I2

sulfuric acid

→

title compound

Ausbeute 89.6%

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

Ausbeute 89.6%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a round-bottom flask was added
2. 2
   TemperaturAfter cooling to ambient temperature
3. 3
   Sonstigethe reaction was carefully quenched with Na2S2O3 (aq., sat.)
4. 4
   ExtraktionThe resulting mixture was extracted with 2×50 mL of ethyl acetate
5. 5
   TrocknenThe combined organic layers were dried (Na2SO4)
6. 6
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle