Ethanol → Ethyl 2-(3-bromophenyl)-2-methylpropanoate

HRID 1765842ノート

反応式

HRID 1765842 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:14].[CH2:18]([OH:20])[CH3:19]>O>[CH2:18]([O:20][C:9](=[O:14])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:12])[CH3:11])[CH3:19]

参加物

5

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 105132942-(3-Bromophenyl)-2-methylpropanenitrile

生成物 1

HCID 12805127Ethyl 2-(3-bromophenyl)-2-methylpropanoate収率 46%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2-(3-bromo-phenyl)-2-methyl-propionitrile (prepared as described by Barlaam et al. J. Med. Chem., 1999, 42, 23, 4890–4908 incorporated herein by reference; 1.4 g, 6.24 mmol) was dissolved in ethanol (40 mL), treated with concentrated sulfuric acid (1 mL) and the resulting reaction mixture was refluxed for 36 h. The reaction mixture was cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230–400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title product as an orange oil (0.77 g, 46%).

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 36 h
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue that

出典と根拠

ORDレコード
ord-fb54644e18954772a6f6410a46b0f92a
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

反応ノート

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