تفاعل #628490

معادلة التفاعل

methyl 2-bromo-4-methylbenzoate

I2

sulfuric acid

→

title compound

المردود 89.6%

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

المردود 89.6%

المذيبات

AcOH

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر