Potassium Carbonate → 5-Phenyl-2-furaldehyde

HRID 1359654Notes

Reaction equation

HRID 1359654 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]1([C:2]2[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 27694205-Phenyl-2-furaldehydeYield 70.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

A solution of 5-bromo-furan-2-carbaldehyde (1.08 g, 6.16 mmol, 1 eq), phenylboronic acid (0.90 g, 7.39 mmol, 1.1 eq), tetrabutylammonium bromide (1.99 g, 6.16 mmol, 1 eq), palladium acetate (30 mg, 0.0.12 mmol 0.02 eq), K2CO3 (2.13 g, 15.4 mmol, 2.5 eq) in water (10 mL) is stirred under nitrogen at room temperature overnight. Upon completion, the reaction mixture turns into a black mass floating in the solution. The reaction is diluted with 40 ML water and extracted with EtOAc (3×100 mL). The organic layers are combined and stirred with charcoal for 30 min, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give an oil. The product is purified by silica gel chromatography using a Biotage Flash 40M column (10% EtOAc/heptane). Yield 70.1%. HRMS (FAB) calculated for C11H8O2+H 173.0603, found 173.0607.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure
  5. customto give an oil
  6. customThe product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-aa40bde627da4313a29cb3b10a6c99af
Source dataset
uspto-grants-2003_07
Patent number
US06599916B2

Reaction notes

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