Hydrochloric Acid → 2-(2-Fluorobenzoyl)-3-thiophenecarboxaldehyde

HRID 256910Notes

Reaction equation

HRID 256910 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16].C(O)C.Cl>O.CCOCC>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([C:5]1[S:6][CH:7]=[CH:8][C:4]=1[CH:3]=[O:2])=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15728739HCID 15728739, compound

Product 1

HCID 128984342-(2-Fluorobenzoyl)-3-thiophenecarboxaldehydeYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 2-(2-fluorobenzoyl)-3-thiophenecarboxaldehyde dimethylacetal was added a solution of absolute ethanol (575 ml) and hydrogen chloride (39 g). The reaction mixture was heated at reflux for 10 mins, with stirring under nitrogen. The solution was cooled to room temperature, diluted with water and ether, and the layers were separated. The aqueous layer was extracted with ether, and the combined organic layers washed with dilute aqueous sodium bicarbonate solution, brine, dried over anhydrous potassium carbonate, filtered and concentrated. The residue was purified by flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes) to afford 20.3 g (27%) of product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 10 mins
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ether
  5. washthe combined organic layers washed with dilute aqueous sodium bicarbonate solution, brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-77ca2075f27848ff8aefcae5c84e23cb
Source dataset
uspto-grants-1993_11
Patent number
US05260319

Reaction notes

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