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

HRID 541308노트

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HRID 541308 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 69844638Methyl 2-bromo-5-iodo-4-methylbenzoate수율 89.6%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e045711f0c8648bfb6adecd963342007
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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