Nitroethane → HCID 66933355, compound

HRID 1170908Notes

Reaction equation

HRID 1170908 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:16]([CH2:19][CH3:20])([O-:18])=[O:17]>>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[C:19]([N+:16]([O-:18])=[O:17])[CH3:20])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 66933355HCID 66933355, compoundYield 75.6%

Conditions

Temperature
4 °C

Procedure

3,4-difluorobenzaldehyde (54 g, 380 mmol), ammonium acetate (19 g, 247 mmol), and 4 Å molecular sieves (54 g) were combined in nitroethane (810 mL) and heated at reflux for 24 hours. The reaction was filtered, and concentrated in vacuo. The resultant mixture was partitioned between ethyl acetate (500 mL) and water (300 mL). The organic phase was separated, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was cooled to 4° C. for 2 hours then ethanol (100 mL) was added to give yellow crystals which were collected by filtration. (57.2 g 75.6% yield). 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H), 7.15-7.25 (m, 2H), 3.7 (t, 1H), 2.4 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated in vacuo
  5. customThe resultant mixture was partitioned between ethyl acetate (500 mL) and water (300 mL)
  6. customThe organic phase was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. additionethanol (100 mL) was added
  12. customto give yellow crystals which
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-72a60233e31b422b8a452454c1b77054
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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