Dimethylformamide → 4-(Dimethoxymethyl)-3-fluorobenzaldehyde

HRID 1281146Notes

Reaction equation

HRID 1281146 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[C:4]([F:13])[CH:3]=1.[O:14]1CCC[CH2:15]1.C([Li])CCC.CN(C)C=O>O>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([CH:15]=[O:14])=[CH:3][C:4]=1[F:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 184268214-Bromo-1-(dimethoxymethyl)-2-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 184268074-(Dimethoxymethyl)-3-fluorobenzaldehydeYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.53 g, 18.2 mmol) in 1 tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 15 mL) and dimethylformamide (2.1 mL, 27 mmol) sequentially at −78° C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted twice with ether. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 Hexane/ethyl acetate) to afford 4-dimethoxymethyl-3-fluorobenzaldehyde (2.26 g, 63%).

Workup

  1. extractionthe mixture was extracted twice with ether
  2. washwashed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (6:1 Hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bb0c0f623eaf41c692d88824682cc209
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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