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

HRID 624307노트

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HRID 624307 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
50 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-d31a8901faf243f2952617c723419f12
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303020B2

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