Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

HRID 78253Notes

Reaction equation

HRID 78253 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:16]=[O:17]>C(OCC)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 117692346-Bromo-3-pyridinecarboxaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a diethyl ether (500 mL) solution of 2,5-dibromopyridine (25 g, 110 mmol) was added dropwise n-butyl lithium (2.67 M n-hexane solution, 45 mL, 120 mmol) at −76° C., which was stirred for 25 minutes. To this solution was added dropwise N,N-dimethylformamide (9.0 mL, 120 mmol) at −76° C. Upon completion of this addition, the reaction solution was gradually cooled to room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1) to obtain the title compound (8.0 g, 41%).

Workup

  1. additionUpon completion of this addition
  2. customThis mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-7217fd09e51141518f1e3d19b0b05fe9
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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