Water → 2-(Difluoromethyl)-4-fluorobenzaldehyde

HRID 85123Notes

Reaction equation

HRID 85123 reaction equation
C([Mg]Br)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[CH:14]([F:16])[F:15].CN(C)[CH:19]=[O:20].O>C1COCC1>[F:15][CH:14]([F:16])[C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 463116681-Bromo-2-(difluoromethyl)-4-fluorobenzeneHCID 178418365HCID 178418365, compound

Product 1

HCID 866522552-(Difluoromethyl)-4-fluorobenzaldehydeYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isopropyl magnesium bromide (30 mL, 1M in THF, 30 mmol) was added dropwise to an ice-cooled solution of 1-bromo-2-(difluoromethyl)-4-fluorobenzene (44; 6 g, 26.7 mmol) in THF (100 mL). The reaction mixture was then allowed to warm to room temperature and stirred for 3 hr. Dimethylformamide (3.5 ml, 45.2 mmol) was added and the reaction stirred for 3 hr. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2-(difluoromethyl)-4-fluorobenzaldehyde 45 (3.2 g, 68.5%)

Workup

  1. stirringthe reaction stirred for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography

Sources & evidence

ORD record
ord-0300ff7b73b7453d8f3bb96c1da31f6a
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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