Hydrochloric Acid → HCID 43554866, compound

HRID 901318Notes

Reaction equation

HRID 901318 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[CH:18]=[C:19]([OH:24])[CH:20]=[CH:21][C:22]=1[F:23].[BH4-].[Na+].Cl>CN(C)C=O.O.C(O)C>[F:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][C:22]=1[F:23])[O:24][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 759273,4-DifluorophenolHCID 4311764Sodium borohydride

Product 1

HCID 43554866HCID 43554866, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 4-fluorobenzaldehyde (2.50 g, 20.1 mmol) in N,N-dimethylformamide (13 mL) were added potassium carbonate (3.33 g, 24.1 mmol) and 3,4-difluorophenol (2.61 g, 20.1 mmol) in turn, and the mixture was stirred for 2.5 hours at 135° C. Water was added to the reaction mixture, which was extracted with ethyl acetate. Then the ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue were added ethanol (50 mL) and sodium borohydride (760 mg, 20.1 mmol) in turn, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture, which was brought to pH 4 with 3 mol/L hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→3:1) to afford 4.40 g of pale yellow liquid title compound. Yield 93%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThen the ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringthe mixture was stirred for 4 hours at room temperature
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→3:1)

Sources & evidence

ORD record
ord-fd769dd1e4044f60a56acfddcab9a39a
Source dataset
uspto-grants-2008_04
Patent number
US07361783B2

Reaction notes

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