Dimethylformamide → 2-(Difluoromethyl)benzaldehyde

HRID 876547Notes

Reaction equation

HRID 876547 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([F:15])[F:14].CN([CH:19]=[O:20])C>C1COCC1>[F:14][CH:13]([F:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27611811-Bromo-2-(difluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 547723942-(Difluoromethyl)benzaldehydeYield 112.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-BuLi (4.2 mL, 10.6 mmol) in THF was added to a solution of 1-bromo-2-(difluoromethyl)benzene 51 (2.0 g, 9.7 mmol) in THF (50 mL) at −78° C. The reaction mixture was stirred for 30 min and DMF (1.4 g, 19.3 mmol) was added. Stirring was continued for 1 h at −40° C. and the reaction was quenched by the addition of sat. aq NH4Cl. The crude mixture was extracted with Et2O, dried (MgSO4) and concentrated to give 52 (1.7 g, 94% yield).

Workup

  1. stirringStirring
  2. waitwas continued for 1 h at −40° C.
  3. customthe reaction was quenched by the addition of sat. aq NH4Cl
  4. extractionThe crude mixture was extracted with Et2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04a8e5cf6fcc435c85016215b6f960e9
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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