Sulfuric Acid → (5-Bromo-4-fluoro-2-methyl-phenyl)-acetic acid methyl ester

HRID 1022385노트

반응식

HRID 1022385 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](Cl)(Cl)Cl)[C:5]([CH3:13])=[CH:4][C:3]=1[F:14].[CH3:15][O-:16].[Na+].S(=O)(=O)(O)[OH:19]>CO>[CH3:15][O:16][C:9](=[O:19])[CH2:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([F:14])=[CH:4][C:5]=1[CH3:13]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 596145891-Bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro-ethyl)-benzene

생성물 1

HCID 59614585(5-Bromo-4-fluoro-2-methyl-phenyl)-acetic acid methyl ester

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
5 °C

실험 절차

To a solution of 1-bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro-ethyl)-benzene (29.2 g) in methanol (100 ml) is added a sodium methoxide solution (30% in methanol, 78.2 ml) dropwise. The reaction mixture is stirred at reflux for 24 hours, cooled to 5° C. and treated with concentrated sulfuric acid (13.2 ml) dropwise. After further warming to reflux for 21 hours, the mixture is concentrated and the residue diluted with water/ethyl acetate. The aqueous layer is extracted with ethyl acetate, the combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3). Yield: 18.76 g of (5-bromo-4-fluoro-2-methyl-phenyl)-acetic acid methyl ester as an oil.

후처리

  1. temperatureat reflux for 24 hours
  2. temperatureAfter further warming
  3. temperatureto reflux for 21 hours
  4. concentrationthe mixture is concentrated
  5. additionthe residue diluted with water/ethyl acetate
  6. extractionThe aqueous layer is extracted with ethyl acetate
  7. washthe combined organic layers are washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3)

출처 및 근거

ORD 기록
ord-6381524a03d04d08a6ce5d06a44d1b80
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722578B2

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