Iodine chloride → Methyl 5-iodo-2-methoxy-4-methylbenzoate

HRID 624307ノート

反応式

HRID 624307 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[I:14]Cl>CO>[I:14][C:10]1[C:11]([CH3:13])=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

4

反応物 2

HCID 24640Iodine chlorideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

生成物 1

HCID 29934724Methyl 5-iodo-2-methoxy-4-methylbenzoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of methyl 2-methoxy-4-methylbenzoate (2.6 g, 14.43 mmol) in methanol (25 ml) at room temperature in a 100 ml round bottomed (RB) flask was added iodine monochloride (3.62 ml, 72.1 mmol) in methanol dropwise. The reaction mixture was heated at 50° C. for 15 hours. The methanol was concentrated, diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic extracts were washed with 0.1N HCl, water and brine solution. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was used for the next step without further purification (3.2 g, 73%). LCMS: (ES+) m/z=307 (M+H)+; Column: ZORBAX SB C18 (4.6×50) mm, 5 μm; Moblie (M) phase A: 10% MeOH-90% H2O-0.1% TFA; Moblie (M) phase B: 90% MeOH-10% H2O-0.1% TFA; Flow: 5 ml/min; Time (min.): 0 2 3; % B: 0 100 0; Retention Time (RT): 1.87 min.

後処理

  1. concentrationThe methanol was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. washThe combined organic extracts were washed with 0.1N HCl, water and brine solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was used for the next step without further purification (3.2 g, 73%)
  9. customRetention Time (RT)
  10. custom1.87 min.

出典と根拠

ORDレコード
ord-d31a8901faf243f2952617c723419f12
出典データセット
uspto-grants-2016_04
特許番号
US09303020B2

反応ノート

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