Water → HCID 117607175, compound

HRID 588842Notes

Reaction equation

HRID 588842 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]=[CH2:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[Cl:19].[OH2:20]>CN(C=O)C.Cl[Pd]Cl>[Cl:19][C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[C:5]([CH2:10][CH:11]=[O:20])[CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 117607167HCID 117607167, compound

Product 1

HCID 117607175HCID 117607175, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,2′,5′-trichloro-4-methoxy-5-vinylbiphenyl (1.0 g, 3.2 mmol) in anhydrous DMF (10 mL), PdCl2 (1.14 g, 6.4 mmol) was added and the resulting mixture was stirred at room temperature under nitrogen for 16 h. To this mixture, water (0.5 mL) was added and the resulting mixture was stirred at room temperature for another 6 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (1-3% ethyl acetate/petroleum ether) to afford the desired product (300 mg, 29% yield) as a white solid.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for another 6 h
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (1-3% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c00b29ade9d84124a28b991e1a71a50a
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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