4-Nitrobenzaldehyde → HCID 23157603, compound

HRID 507930Notes

Reaction equation

HRID 507930 reaction equation
Br[C:2]([F:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11].S([O-])(O)(=O)=O.[Na+]>O1CCCC1.[Zn]>[F:8][C:2]([F:9])([CH:17]([OH:18])[C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:20][CH:19]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 69585Ethyl bromodifluoroacetateHCID 516919Sodium Bisulfate

Product 1

HCID 23157603HCID 23157603, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl bromodifluoroacetate (20.3 g, 100 mmol) and zinc powder (6.5 g, 100 mmol) in tetrahydrofuran (100 mL) was heated under reflux for 10 min, and 4-nitrobenzaldehyde (8.4 g, 55.8 mmol) was added dropwise. The reaction mixture was refluxed for 4 hr and allowed to cool to room temperature. Aqueous sodium hydrogensulfate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (4.80 g, yield 20%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 min
  3. temperatureThe reaction mixture was refluxed for 4 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-511b7004c453460fbb39162a71e3dadc
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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