Tetrahydrofuran → 6-Bromo-2,3'-bipyridine
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]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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-f8478495cbd744ee8c9098f2ee42001d
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964293B2
Reaction notes
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