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

HRID 2070029Notes

Reaction equation

HRID 2070029 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-41d60ad3953644c4b04ae802bfc04e5a
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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