2-Nitrobenzaldehyde → HCID 15673275, compound

HRID 1838100Notes

Reaction equation

HRID 1838100 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][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])([O-:12])=[O:11]>C1COCC1.CCOC(C)=O.[Zn]>[CH2:6]([O:5][C:3](=[O:4])[C:2]([F:9])([F:8])[CH:15]([C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[N+:10]([O-:12])=[O:11])[OH:16])[CH3:7]

Participants

6

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 15673275HCID 15673275, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a slurry of activated zinc (6.25 g, 99.2 mmol) in 75 mL anhydrous THF, was added ethyl bromodifluoroacetate (11.0 mL, 85.8 mmol) and the mixture was heated to reflux. After a visible reaction had occurred, 2-nitrobenzaldehyde (5.0 g, 33.1 mmol) in 30 mL anhydrous THF, was added dropwise to maintain reflux. After 3 h, the solution was cooled to 23° C., diluted with EtOAc (50 mL), washed with 1M KHSO4 (2×50 mL) and brine (1×50 mL), and dried (Na2SO4). Concentration in vacuo yielded a residue which was purified by flash chromatography (chloroform:EtOH, 99:1) to afford 2-(3-ethoxy-3-oxo-2,2-difluoro-1-hydroxypropyl)nitrobenzene (8.28 g, 91%) as an orange 30 oil, which was taken on to the next step without further characterization.

Workup

  1. temperaturethe mixture was heated to reflux
  2. customAfter a visible reaction
  3. temperatureto maintain
  4. temperaturereflux
  5. washwashed with 1M KHSO4 (2×50 mL) and brine (1×50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration in vacuo
  8. customyielded a residue which
  9. customwas purified by flash chromatography (chloroform:EtOH, 99:1)

Sources & evidence

ORD record
ord-b5f0f12a3d884a3eb6fcd4cec36a5aec
Source dataset
uspto-grants-2004_01
Patent number
US06673788B2

Reaction notes

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