Acetonitrile → 1-[2-Amino-5-bromo-4-(trifluoromethyl)phenyl]ethanone

HRID 69114ノート

反応式

HRID 69114 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(#N)C.[Br:18]N1C(=O)CCC1=O>C(OCC)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[C:5]([Br:18])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 468355001-(2-Amino-4-(trifluoromethyl)phenyl)ethan-1-one

生成物 1

HCID 666961351-[2-Amino-5-bromo-4-(trifluoromethyl)phenyl]ethanone収率 64.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a mixture of 11.6 g of 1-[2-amino-4-(trifluoromethyl)phenyl]ethanone, 60 mL of acetonitrile, and 230 mL of diethyl ether was added 2.85 g of Amberlyst (registered trademark) 15, and 10.1 g of N-bromosuccinimide was added thereto in three times in an ice bath. After stirring for 30 minutes in an ice bath, the mixture was stirred at room temperature overnight. The insoluble material was filtered and washed with ethyl acetate. To the filtrate were added water and ethyl acetate, and the aqueous layer was separated. The organic layer was washed with a 10% aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate, and then solvent was evaporated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 10.36 g of 1[2-amino-5-bromo-4-(trifluoromethyl)phenyl]ethanone.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature overnight
  3. filtrationThe insoluble material was filtered
  4. washwashed with ethyl acetate
  5. additionTo the filtrate were added water and ethyl acetate
  6. customthe aqueous layer was separated
  7. washThe organic layer was washed with a 10% aqueous sodium thiosulfate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customsolvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-195fbe543fdd481195764ad9f4a660d0
出典データセット
uspto-grants-2014_09
特許番号
US08822448B2

反応ノート

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