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

HRID 1962373ノート

反応式

HRID 1962373 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
5 °C

実験手順

To a solution of 1-bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro-ethyl)-benzene (29.2 g) in methanol (100 ml) was added a sodium methoxide solution (30% in methanol, 78.2 ml) dropwise. The reaction mixture was 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 was concentrated and the residue diluted with water/ethyl acetate. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was 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.

後処理

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

出典と根拠

ORDレコード
ord-62db5efd29ae48b7a130db8f1ca5b702
出典データセット
uspto-grants-2013_04
特許番号
US08415369B2

反応ノート

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