2,5-Dibromopyridine → 5,5'-DIBROMO-2,2'-BIPYRIDINE

HRID 388185Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C(C)=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A reaction vessel was charged with 6.0 g of 2,5-dibromopyridine, 7.0 ml of bistributyltin, and 120 ml of xylene, followed by heating and stirring at 60° C. for 15 minutes. Further, 700 mg of tetrakis(triphenylphosphine)palladium was added thereto, followed by stirring at 120° C. for 8 hours. After cooling to room temperature, the insoluble materials were removed by filtration, and the filtrate was washed with 150 ml of an aqueous ethylenediamine tetraacetate solution. The organic layer was dehydrated with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: cyclohexane/toluene) to obtain 1.7 g (yield 42%) of 5,5′-dibromo-[2,2′]bipyridine as a yellow powder.

Workup

temperatureby heating
stirringby stirring at 120° C. for 8 hours
temperatureAfter cooling to room temperature
customthe insoluble materials were removed by filtration
washthe filtrate was washed with 150 ml of an aqueous ethylenediamine tetraacetate solution
concentrationconcentrated under reduced pressure
customto obtain a crude product
customThe crude product was purified by column chromatography (carrier: silica gel, eluent: cyclohexane/toluene)

Sources & evidence

ORD record: ord-1ba185198f794398a9b7d1fc760388af
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377573B2

Reaction notes

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