Nitroethane → 1,2,4,5-Tetrafluoro-3-(2-nitroprop-1-enyl)benzene

HRID 69330

Reaction equation

HRID 69330 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[C:6]([F:12])[C:3]=1[CH:4]=O.[N+:13]([CH2:16][CH3:17])([O-:15])=[O:14].C1(N)CCCCC1>C(O)(=O)C>[F:11][C:7]1[CH:8]=[C:9]([F:10])[C:2]([F:1])=[C:3]([CH:4]=[C:16]([N+:13]([O-:15])=[O:14])[CH3:17])[C:6]=1[F:12]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 7965CyclohexylamineHCID 6013312,3,5,6-Tetrafluorobenzaldehyde

Product 1

HCID 866632051,2,4,5-Tetrafluoro-3-(2-nitroprop-1-enyl)benzeneYield 91.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,3,5,6-tetrafluorobenzaldehyde (25.0 g, 0.14 mol), nitroethane (21.08 g, 0.28 mol), and cyclohexylamine (13.92 g, 0.14 mol) in 150 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to room temperature (rt) and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 30.0 g (91%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 258.0 [M+Na]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature (rt)
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate three times
  5. dry with materialThe combined extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customProduct was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-8a63e1d89d654179884ad2e4fd5a9ac9
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Linked notes

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