Tetrahydrofuran → 6-Bromo-2,3'-bipyridine

HRID 221179Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.C1COCC1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[N:20]=1>C1(C)C=CC=CC=1.CN(C)CCN(C)C.[Cl-].[Zn+2].[Cl-].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>[Br:25][C:21]1[N:20]=[C:19]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen atmosphere, 6.32 g of 3-bromopyridine was dissolved in 400 ml of dehydrated toluene. The solution was cooled at −78° C. and 17 ml of 2.6M normal-butyllithium was dropped. After 0.5 hours, 12.6 g of zinc chloride tetramethylethylenediamine, and 200 ml of dehydrated THF were added. The solution was heated to room temperature, 10.63 g of 2,6-dibromopyridine and 0.6 g of Pd(PPh3)4 were added, and the solution was stirred for 24 hours. The reaction liquid was washed by an ammonium chloride aqueous solution, and the organic layer was concentrated in an evaporator. The concentrates were purified by column chromatography, and thus 4.2 g of 6-bromo-2,3′-bipyridine was obtained.

Workup

temperatureThe solution was heated to room temperature
customThe reaction liquid
washwas washed by an ammonium chloride aqueous solution
concentrationthe organic layer was concentrated in an evaporator
customThe concentrates were purified by column chromatography

Sources & evidence

ORD record: ord-fa783822116942fe8bc4a2cbd7be8b58
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202633B2

Reaction notes

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