Water → Ethyl 2-(3-fluorophenoxy)-2-methylpropanoate

HRID 56274ノート

反応式

HRID 56274 の反応式
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

生成物 1

HCID 58243746Ethyl 2-(3-fluorophenoxy)-2-methylpropanoate収率 47.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 3-fluorophenol (3.36 g, 30.0 mmol), ethyl 2-bromo-2-methylpropanoate (8.78 g, 45.0 mmol) and K2CO3 (6.22 g, 45.0 mmol) in acetone (50 mL) was refluxed overnight. The mixture was cooled to rt and 60 mL of water was added. The resulting mixture was extracted with DCM (40 mL×2). The combined organic phases were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless liquid (3.20 g, 47%).

後処理

  1. temperaturewas refluxed overnight
  2. extractionThe resulting mixture was extracted with DCM (40 mL×2)
  3. washThe combined organic phases were washed with brine (40 mL×2)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

出典と根拠

ORDレコード
ord-aa565b51f54e4f788b914aab720434e4
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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