2,6-Dibromopyridine → 2-Acetyl-6-bromopyridine

HRID 1952865Notes

Reaction equation

HRID 1952865 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Li])CCC.CN(C)[C:16](=[O:18])[CH3:17]>C(OCC)C>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:16](=[O:18])[CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 31374DimethylacetamideHCID 178418339Butyllithium

Product 1

HCID 112985782-Acetyl-6-bromopyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

29.7 g of 2,6-dibromopyridine were reacted with 86.1 ml of n-butyllithium (1.6-molar solution in n-hexane) and 12 g of N,N-dimethylacetamide in 300 ml of diethyl ether as described in the literature [J. Organomet. Chem. 56 (1973), 53-66; Chem. Ber. 125 (1992), 1169-1190] to give 2-bromo-6-acetylpyridine.

Sources & evidence

ORD record
ord-f3e4b6f9576e42ffa83a428cb564c49e
Source dataset
uspto-grants-2000_09
Patent number
US06114363

Reaction notes

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