Potassium Acetate → HCID 86636417, compound

HRID 1664326Notes

Reaction equation

HRID 1664326 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH:15]=[O:16])=[CH:4][C:3]=1[CH2:19][O:20]C1CCCCO1.[B:27]1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)[O:28]1.C([O-])(=O)C.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]3[B:27]([OH:28])[O:20][CH2:19][C:3]=3[CH:4]=2)=[C:8]([CH:15]=[O:16])[CH:9]=1)#[N:12]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 86636416HCID 86636416, compound

Product 1

HCID 86636417HCID 86636417, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[4-bromo-3-(2-tetrahydropyranyloxymethyl)phenoxy]-3-formylbenzonitrile (28.0 g, 67.3 mmol), bis(pinacolato)diboron (18.8 g, 74.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.37 g, 2.5 mol %), and potassium acetate (19.8 g, 202 mmol) in 1,4-dioxane (270 mL) was stirred under nitrogen atmosphere at 80° C. overnight. The mixture was filtered through a Celite pad, and the solvent was removed under reduced pressure. The residue was dissolved in tetrahydrofuran (250 mL) and was added 6 M HCl (30 mL), and the mixture was stirred at room temperature for 2 h. The mixture was poured into ethyl acetate/water. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column (5:5 to 3:7 hexane/ethyl acetate) followed by recrystallization from ethyl acetate/hexane to give 5-(4-cyano-2-formylphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (6.61 g, 35%).

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (250 mL)
  4. additionwas added 6 M HCl (30 mL)
  5. stirringthe mixture was stirred at room temperature for 2 h
  6. additionThe mixture was poured into ethyl acetate/water
  7. washThe organic layer was washed with brine
  8. dry with materialdried on anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by silica gel column (5:5 to 3:7 hexane/ethyl acetate)
  11. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5e42871acd324e1b8d8b44a8711c8bd8
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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