Hydrochloric Acid → 2-Fluoro-4-nitrobenzaldehyde

HRID 2265105Notes

Reaction equation

HRID 2265105 reaction equation
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[F:14].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl>O1CCCC1>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:15])=[C:6]([F:14])[CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 231065432-Fluoro-n-methoxy-n-methyl-4-nitrobenzamideHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 45629192-Fluoro-4-nitrobenzaldehydeYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 14a (860 mg) was dissolved in tetrahydrofuran (10.0 ml), and the reaction mixture was ice-cooled. Diisobutylaluminum hydride/toluene solution (0.98 mol/l, 5.0 ml) was added thereto, and the mixture was stirred under ice-cooling for 1 hour. After adding a 1N hydrochloric acid aqueous solution, the reaction mixture was returned to room temperature and extracted with ethyl acetate. The organic layer was washed with a 1N hydrochloric acid aqueous solution and saturated sodium-hydrogencarbonate aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was recrystallized with a mixed solvent of tert-butylmethylether and n-heptane to obtain Compound 14b (554 mg, 86%) as a white solid.

Workup

  1. temperaturecooled
  2. temperaturecooling for 1 hour
  3. customwas returned to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a 1N hydrochloric acid aqueous solution and saturated sodium-hydrogencarbonate aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe obtained residue was recrystallized with a mixed solvent of tert-butylmethylether and n-heptane

Sources & evidence

ORD record
ord-630217ffade746f0bb9e3ce40ff16cea
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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