Cesium carbonate → Biphenyl

HRID 2078461Notes

Reaction equation

HRID 2078461 reaction equation
O1[CH2:5][CH2:4][CH2:3]N1.B(O)O.O[C:10]([C:13](O)([CH3:15])[CH3:14])([CH3:12])[CH3:11].[C:17]([O-])(=O)[CH3:18].[K+].[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.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:10]1([C:13]2[CH:15]=[CH:18][CH:17]=[CH:22][CH:14]=2)[CH:12]=[CH:5][CH:4]=[CH:3][CH:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136333IsoxazolidineHCID 517044Potassium AcetateHCID 178459139HCID 178459139, compound

Product 1

HCID 7095BiphenylYield 218.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Isoxazolidine 215 (302 mg, 0.505 mmol), pinacol boronate 49 (368 mg, 1.26 mmol), Pd(dppf)Cl2 (82 mg, 0.101 mmol), potassium acetate (65 mg, 0.657 mmol), and cesium carbonate (494 mg, 1.52 mmol) were dissolved in anhydrous DMSO (5 mL) and flushed under positive argon pressure. The reaction mixture was stirred at 60° C. for 2 h, then allowed to cool to ambient temperature. The reaction mixture was diluted with EtOAc (20 mL) and water (10 mL) and the aqueous phase was adjusted to pH 4 with 6M HCl. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organics were dried (MgSO4), filtered and concentrated to an oil. The crude oil was purified by gradient flash chromatography (10-35% Acetone/hexanes) to afford 170 mg (53%) of biphenyl acid 216.

Workup

  1. customflushed under positive argon pressure
  2. temperatureto cool to ambient temperature
  3. additionThe reaction mixture was diluted with EtOAc (20 mL) and water (10 mL)
  4. extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe crude oil was purified by gradient flash chromatography (10-35% Acetone/hexanes)

Sources & evidence

ORD record
ord-dfb3a10418d24f609fd86342085efb57
Source dataset
uspto-grants-2011_04
Patent number
US07928244B2

Reaction notes

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