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

HRID 541308

反応式

HRID 541308 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 69844638Methyl 2-bromo-5-iodo-4-methylbenzoate収率 89.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e045711f0c8648bfb6adecd963342007
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

関連ノート

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