Nitroethane → 1-(2,5-Difluorophenyl)-2-nitropropene

HRID 69328

Reaction equation

HRID 69328 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C1(N)CCCCC1>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 7965CyclohexylamineHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 666905281-(2,5-Difluorophenyl)-2-nitropropeneYield 81.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,5-difluorobenzaldehyde (25.0 g, 0.176 mol), nitroethane (26.41 g, 0.352 mol) and cyclohexylamine (17.45 g, 0.176 mol) in 150 mL of acetic acid was stirred at 80° C. overnight. After cooling to rt the solvent was evaporated, the residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v) to give a yellow solid product, 28.5 g, 81.3% yield. MS: 197.6 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 7.94 (s, 1H), 7.46-7.43 (m, 1H), 7.41-7.35 (m, 2H), 2.31 (s, 3H).

Workup

  1. temperatureAfter cooling to rt the solvent
  2. customwas evaporated
  3. customthe residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v)
  4. customto give a yellow solid product, 28.5 g, 81.3% yield

Sources & evidence

ORD record
ord-1c9a8319490d48369f38e5846bbd8c50
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Linked notes

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