Nitroethane → 4-Fluoro-1-methyl-2-(2-nitroprop-1-enyl)benzene

HRID 920457Notes

Reaction equation

HRID 920457 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH:7]=O.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C1(N)CCCCC1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:7]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15])[CH:9]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 7965CyclohexylamineHCID 27590125-Fluoro-2-methylbenzaldehyde

Product 1

HCID 666905114-Fluoro-1-methyl-2-(2-nitroprop-1-enyl)benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-2-methylbenzaldehyde (50.0 g, 0.382 mol), nitroethane (54.34 g, 0.724 mol), and cyclohexylamine (35.90 g, 0.382 mol) in 300 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 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 62.8 g (89%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 217.9 [M+Na]+.

Workup

  1. temperaturethe reaction mixture was cooled to 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-143de7766ba14dd3a06dd241d6937388
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

Loading…