Potassium Carbonate → HCID 68431677、化合物

HRID 889242ノート

反応式

HRID 889242 の反応式
[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([F:17])[C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>CN(C=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][NH:11][C:10]1[C:12]([F:17])=[CH:13][C:14]([Br:16])=[CH:15][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2 回HCID 684315652-(Benzyloxy)-4-bromo-6-fluoroaniline

生成物 1

HCID 68431677HCID 68431677、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 2.6 g (8.78 mmol) of 2-benzyloxy-4-bromo-6-fluoroaniline and 3.03 g (21.96 mmol) of potassium carbonate in 20 mL DMF in an oil bath at 60° C. is added 1.48 g (9.67 mmole) of methyl bromoacetate. The mixture is stirred at 60° C. for 2 h. HPLC analysis indicated that the reaction is 38% complete. Additional methyl bromoacetate equal to the molar amount of unreacted starting material is added and the mixture is stirred at 60° C. for 2 h. This process is repeated until the starting material is nearly consumed. The mixture is allowed to cool then is poured into water. The mixture is extracted with ethyl acetate and the organic phase is washed 3× with water. The organic solution is dried over sodium sulfate and the solvent is removed under reduced pressure. The residual dark oil is purified by flash chromatography using methylene chloride to elute the product as a dark oil. This is used directly in the next step.

後処理

  1. additionis added
  2. stirringthe mixture is stirred at 60° C. for 2 h
  3. customis nearly consumed
  4. temperatureto cool
  5. additionthen is poured into water
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe organic phase is washed 3× with water
  8. dry with materialThe organic solution is dried over sodium sulfate
  9. customthe solvent is removed under reduced pressure
  10. customThe residual dark oil is purified by flash chromatography
  11. washto elute the product as a dark oil

出典と根拠

ORDレコード
ord-ddde81f4844044b7b1dd97e59431e00c
出典データセット
uspto-grants-2012_08
特許番号
US08252820B2

反応ノート

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