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

HRID 2070029

반응식

HRID 2070029 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-41d60ad3953644c4b04ae802bfc04e5a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299252B2

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