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

HRID 555177노트

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HRID 555177 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

Methyl 2-methoxy-4-methylbenzoate (1.5 g, 8.32 mmol, 1 eq) was dissolved in methanol. To this solution was added dropwise iodine monochloride (6.75 g, 41.6 mmol, 5 eq) in methanol at room temperature. The reaction mixture was heated at 50° C. for 15 h. Finally, methanol was concentrated, diluted with water and extracted with ethyl acetate. The organic layer was washed with 0.1 N HCl (50 ml), water (100 ml) and brine solution (100 ml). The product was purified by column chromatography using 60-120 silica gel and using 5% ethyl acetate/hexane as eluent. Yield: 1.7 g (80%). 1H NMR (400 MHz, CDCl3): δ 2.44 (s, 3H), 3.86 (s, 3H), 3.88 (s, 3H), 6.86 (s, 1H), 8.20 (s, 1H). LCMS: (ES+) m/z=307.0 (M+H).

후처리

  1. concentrationFinally, methanol was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 0.1 N HCl (50 ml), water (100 ml) and brine solution (100 ml)
  5. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-6d75db834f894954bfb04fcc3d6cccf1
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048887B2

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