Phenylboronic Acid → HCID 17764610, compound

HRID 2121711Notes

Reaction equation

HRID 2121711 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([Cl:10])[S:6][C:5]=1Cl)(=[O:3])[CH3:2].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([Cl:10])[S:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 12112791HCID 12112791, compound

Product 1

HCID 17764610HCID 17764610, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 3-acetyl-2,5-dichloro-4-methylthiophene (0.98 g, 4.69 mmol) in DME (15 mL) were added benzeneboronic acid (0.69 g, 7.09 mmol), a saturated aqueous solution of sodium bicarbonate (5 mL) and bis(triphenylphosphine)palladium(II)chloride (0.39 g, 0.56 mmol) at room temperature under nitrogen. The mixture was heated at reflex temperature for 3 hours. The whole was extracted with diethyl ether (50 mL×2), and the combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (10:1) to provide the title product (916 mg, 78% yield ).

Workup

  1. customat room temperature
  2. temperatureThe mixture was heated at reflex temperature for 3 hours
  3. extractionThe whole was extracted with diethyl ether (50 mL×2)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-dd8bdca59736446fb1ec2dfcfcc277e4
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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