Potassium Acetate → HCID 22171517, compound

HRID 1866152Notes

Reaction equation

HRID 1866152 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[C:9]([CH3:15])[C:8]=1[CH3:16])(=O)=O.[B:19]1(B2OC(C)(C)C(C)(C)O2)[O:23]C(C)(C)C(C)(C)[O:20]1.C([O-])(=O)C.[K+]>O1CCOCC1.C(OCC)(=O)C.O>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([B:19]([OH:23])[OH:20])=[C:8]([CH3:16])[C:9]=1[CH3:15])=[O:14]

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 109679582,3-dimethyl-4-trifluoromethanesulfonyloxybenzaldehyde

Product 1

HCID 22171517HCID 22171517, compoundYield 35.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-formyl-2,3-dimethylphenyl trifluoromethanesulfonate (2.5 g) in 1,4-dioxane (50 ml) was added bis(pinacolato)diboron (2.47 g), 1,1′-bis(diphenyl-phosphino)ferrocene-palladium(II)dichloridedichloromethane complex (1:1) (1.09 g) and potassium acetate (2.61 g), and the mixture was stirred at 90° C. for 5 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated. To a suspension of the crude product in acetone (80 ml) and water (80 ml) was added ammonium acetate (1.4 g) and sodium periodate (3.95 g), and the mixture was stirred at room temperature for 6 hours. The solvent was evaporated, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1) to give (4-formyl-2,3-dimethylphenyl)boronic acid (560 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with 1N hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionTo a suspension of the crude product in acetone (80 ml) and water (80 ml)
  6. additionwas added ammonium acetate (1.4 g) and sodium periodate (3.95 g)
  7. stirringthe mixture was stirred at room temperature for 6 hours
  8. customThe solvent was evaporated
  9. additionthe mixture was diluted with ethyl acetate
  10. customThe organic layer was separated
  11. washwashed with water and brine
  12. dry with materialdried over magnesium sulfate
  13. customevaporated under reduced pressure
  14. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-9b4df97cd6f34b64bb60525ce5e60ecd
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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