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

HRID 1022385ノート

反応式

HRID 1022385 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) 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.

後処理

  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)

出典と根拠

ORDレコード
ord-6381524a03d04d08a6ce5d06a44d1b80
出典データセット
uspto-grants-2014_05
特許番号
US08722578B2

反応ノート

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