Hydrochloric Acid → Ethyl 2-(4-chloro-2-fluorophenyl)-2-formylacetate

HRID 1870789Notes

Reaction equation

HRID 1870789 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([F:16])[CH:5]=1.[CH:17](OCC)=[O:18].Cl>O1CCCC1.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:17]=[O:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([F:16])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 4518464Ethyl 4-chloro-2-fluorophenylacetate

Product 1

HCID 21200432Ethyl 2-(4-chloro-2-fluorophenyl)-2-formylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Then, 3.6 g of sodium hydride (60% in oil) was suspended in 120 ml of tetrahydrofuran, and the mixture was cooled to 5° C., to which a solution of 17.8 g of ethyl 4-choro-2-fluorophenylacetate in 120 ml of tetrahydrofuran was slowly added drop-wise. The mixture was stirred for 30 minutes with a gradual temperature increase to room temperature, to which 20 ml of ethyl formate was added at room temperature, followed by stirring for 3 hours. Then, the reaction mixture was cooled with ice, to which diluted aqueous hydrochloric acid was added. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 19.1 g of ethyl 2-(4-chloro-2-fluorophenyl)-2-formylacetate.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring for 3 hours
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af3f328fd9524eb0bb67f082dbe348d7
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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