Dimethylformamide → 5-(Dimethoxymethyl)-2-fluorobenzaldehyde

HRID 503108Notes

Reaction equation

HRID 503108 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6](Br)[CH:5]=1.C([Li])CCC.CN(C)[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH:5]=1)[CH:21]=[O:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 222608642-Bromo-4-(dimethoxymethyl)-1-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 222607045-(Dimethoxymethyl)-2-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A total of 2.49 g of 3-bromo-4-fluorobenzaldehyde dimethylacetal produced in Production Example I-4-a was dissolved in 20 ml of dry tetrahydrofuran. After cooling to −78° C. in an atmosphere of nitrogen gas, 8.5 ml of a 1.56 M solution of n-butyllithium in hexane was added. After stirring for 30 minutes, 1.0 ml of N,N-dimethylformamide was added and the mixture was heated to room temperature. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate for two times. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:12.5), to give 1.35 g of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate for two times
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:12.5)

Sources & evidence

ORD record
ord-3e8a4ea503104e0b96d6c886ed63ffd8
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

Loading…