Fluorobenzene → HCID 18330548, compound

HRID 1656853Notes

Reaction equation

HRID 1656853 reaction equation
[F:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1I.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>Cl[Pd]Cl.[Pd].C([O-])([O-])=O.[Na+].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 10008FluorobenzeneHCID 27245164-Bromo-2-fluoro-1-iodobenzene

Product 1

HCID 18330548HCID 18330548, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24290Palladium ChlorideCatalystHCID 10340Sodium CarbonateSolvent

Procedure

3 g of 2-fluoro-4-bromoiodobenzene, about 0.4 g of PdCl2 and 0.2 g or 5% Pd on carbon, 20 ml of fluorobenzene, and 10 ml of 2M Na2CO3, were added to a 3-neck round bottom flask equipped with a slow nitrogen purge. The mixture was vigorously stirred and 1.21 g of phenylboronic acid in about 5 g of concentrated ethanol was added. The solution was then refluxed at 70°-72° C. The resulting solution was then analyzed by gas chromatography (corrected for sensitivity factors) and it was determined that the desired product, 2-fluoro-4-bromobiphenyl, was produced in 55% yield with about 12% fluoroterphenyl.

Workup

  1. customequipped with a slow nitrogen
  2. custompurge
  3. addition1.21 g of phenylboronic acid in about 5 g of concentrated ethanol was added
  4. temperatureThe solution was then refluxed at 70°-72° C

Sources & evidence

ORD record
ord-aa3d58ea98ec4003926c8bc6388144c6
Source dataset
uspto-grants-1993_10
Patent number
US05254776

Reaction notes

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