Allyl Alcohol → 3-(4-Nitro-2-(trifluoromethyl)phenyl)propionaldehyde

HRID 2070029

反応式

HRID 2070029 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([OH:18])[CH:16]=[CH2:17].C(N(CC)CC)C>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:17][CH2:16][CH:15]=[O:18])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

参加物

7

反応物 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 1361982-Bromo-5-nitrobenzotrifluoride

生成物 1

HCID 231552963-(4-Nitro-2-(trifluoromethyl)phenyl)propionaldehyde収率 69%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

4-Bromo-3-(trifluoromethyl)nitrobenzene (2700 mg, 10 mmol) was dissolved in DMF (15 mL), and allyl alcohol (1750 mg, 30 mmol), tetrabutylammonium chloride (2780 mg, 10 mmol), palladium acetate (120 mg, 5 mol %), and triethylamine (3 mL, 21 mmol) were added thereto. The resulting mixture was stirred under argon atmosphere at 90° C. for 0.5 hours. The reaction solution was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=4:1) to give 3-(4-nitro-2-(trifluoromethyl)phenyl)propionaldehyde (1700 mg, 69%) as a light-yellow oil.

後処理

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-41d60ad3953644c4b04ae802bfc04e5a
出典データセット
uspto-grants-2012_10
特許番号
US08299252B2

関連ノート

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