5-Bromo-2,1,3-benzoxadiazole → 5-Ethenyl-2,1,3-benzoxadiazole

HRID 1502053Notes

Reaction equation

HRID 1502053 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.[CH:11]([B-](F)(F)F)=[CH2:12].[K+]>CCO.CCOC(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]>[CH:11]([C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1)=[CH2:12]

Participants

6

Reactant 2

HCID 27762985-Bromo-2,1,3-benzoxadiazoleHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 595687205-Ethenyl-2,1,3-benzoxadiazole

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5-bromo-2,1,3-benzoxadiazole (4.0 g, 20 mmol), potassium vinyltrifluoroborate (5.40 g, 40.2 mmol) and Pd(dppf)Cl2 (1.6 g, 2 mmol) in TEA (5.2 mL) and EtOH (15 mL) were added to a flask containing a stir bar, and the flask was then heated at 80° C. for 12 h. The organic residue was dissolved in EtOAc (500 mL) and the solution was washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting organic residue was subjected to purification over silica gel to give the title compound.

Workup

  1. additioncontaining a stir bar
  2. washthe solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting organic residue was subjected to purification over silica gel

Sources & evidence

ORD record
ord-d5b2287e445a456ea9b27d38ab01eb37
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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