Water → 2-Fluoro-4-nitrobenzaldehyde

HRID 2080673Notes

Reaction equation

HRID 2080673 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[BH4-].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 45629192-Fluoro-4-nitrobenzaldehydeYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

43.3 g of 2-fluoro-4-nitrobenzoic acid was dissolved in 600 ml of dimethylformamide, and 1,1′-carbodiimide was added to it, and stirred at room temperature for 2 hours. 11.1 g of sodium borohydride was added thereto, and further stirred for 30 minutes. Aqueous saturated ammonium chloride solution was added to it, 800 ml of water was added thereto, extracted with 1.2 liters of ethyl acetate, and the organic layer was washed with saturated saline water. The solvent was evaporated away under reduced pressure, the residue was again diluted with ethyl acetate, and the organic layer was washed with water and saturated saline water. This was dried with anhydrous sodium sulfate, and the solvent was evaporated away to obtain 32.7 g of a brown oil.

Workup

  1. stirringfurther stirred for 30 minutes
  2. additionwas added
  3. extractionextracted with 1.2 liters of ethyl acetate
  4. washthe organic layer was washed with saturated saline water
  5. customThe solvent was evaporated away under reduced pressure
  6. additionthe residue was again diluted with ethyl acetate
  7. washthe organic layer was washed with water and saturated saline water
  8. dry with materialThis was dried with anhydrous sodium sulfate
  9. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-e6793113443d4aeabd21a423194f87e0
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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