Dinitrofluorobenzene → HCID 21999221, compound

HRID 1976847Notes

Reaction equation

HRID 1976847 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.[CH2:21]([OH:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C(=O)C>[CH2:21]([O:31][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 81741-DecanolHCID 8471Triethylamine

Product 1

HCID 21999221HCID 21999221, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a 1 liter flask were charged 1-fluoro-2,4-dinitrobenzene (40.94 g, 0.22 mol), triethylamine (24.29 g, 0.24 mol), 1-decanol (34.82 g, 0.22 mol), 220 g of N,N-dimethylacetamide and stirred at room temperature for 24 hours under a nitrogen atmosphere. The resultant etherified product was extracted with 1 liter of ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain crude product. Isolation and purification of the target product by silica gel chromatography afforded 57.80 g (yield: 81%) of 4-decyloxy-1,3-dinitrobenzene as yellow crystals.

Workup

  1. extractionwas extracted with 1 liter of ethyl acetate
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customto obtain crude product
  5. customIsolation and purification of the target product by silica gel chromatography

Sources & evidence

ORD record
ord-49038fcff85d4298b1b91a54b40f4eba
Source dataset
uspto-grants-2001_05
Patent number
US06228972B1

Reaction notes

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