Nitromethane → 1-benzyloxy-3-fluoro-5-((E)-2-nitro-vinyl)-benzene

HRID 20441Notes

Reaction equation

HRID 20441 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([F:17])[CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:18]([CH3:21])([O-:20])=[O:19].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:21]/[N+:18]([O-:20])=[O:19])[CH:14]=[C:15]([F:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 74892046HCID 74892046, compound

Product 1

HCID 685603091-benzyloxy-3-fluoro-5-((E)-2-nitro-vinyl)-benzeneYield 68.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Heat 3-benzyloxy-5-fluoro-benzaldehyde (3.75 g, 16.29 mmol), nitromethane (4.08 g, 66.79 mmol), and ammonium acetate (3.47 g, 44.96 mmol) in acetic acid (54 mL) in 125° C. oil bath under nitrogen for 4 hours. Cool to room temperature and pour into ice/water. Extract with hexanes/ethyl acetate. Dry (magnesium sulfate), filter and concentrate. Purify on 120 g silica gel eluting with 100:0 to 80:20 hexanes:ethyl acetate to give 3.05 g (68.5%) of the desired compound as a yellow oil.

Workup

  1. extractionExtract with hexanes/ethyl acetate
  2. dry with materialDry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify on 120 g silica gel eluting with 100:0 to 80:20 hexanes

Sources & evidence

ORD record
ord-56c0ab958dbe42dcbe4e9c018cf2c7b4
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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