Hydrochloric Acid → HCID 22260702, compound

HRID 503105Notes

Reaction equation

HRID 503105 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:11])[CH:9]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[F:19][C:7]1[CH:6]=[CH:5][C:4]([CH:3]=[O:2])=[CH:9][C:8]=1[C:10](=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22260789HCID 22260789, compound

Product 1

HCID 22260702HCID 22260702, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 18.7 g of [5-(dimethoxymethyl)-2-fluorophenyl](3-fluorophenyl)methanone was dissolved in 100 ml of tetrahydrofuran, and 5 ml of 5 N hydrochloric acid was added, followed by stirring at room temperature for 1 hour. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate 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, to give 15.8 g of 4-fluoro-3-(3-fluorobenzoyl)benzaldehyde as a colorless oil. A total of 13.8 g of this compound was dissolved in 50 ml of dimethyl sulfoxide, and a solution of 15.2 g of sodium chlorite in 50 ml water was added dropwise over 1 hour under ice-cooling. To the reaction mixture was added diluted hydrochloric acid, 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 filtered using diisopropyl ether, to give 12.9 g of 4-fluoro-3-(3-fluorobenzoyl)benzoic acid as a colorless solid. A total of 11.1 g of this compound was dissolved in 50 ml of N,N-dimethylformamide, and 5.8 g of potassium carbonate and 2.9 ml of methyl iodide were added, followed by stirring at room temperature for 12 hours. To the reaction mixture was added water, 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=1:15), to give 11.5 g of the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate for two times
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fb29b2cd78d84bb79b820cea2fab844e
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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