Dimethylformamide → 5-Bromopyridine-2-carbaldehyde

HRID 2105267Notes

Reaction equation

HRID 2105267 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.CN([CH:17]=[O:18])C.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:17]=[O:18])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 98775625-Bromopyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2,5-dibromopyridine (1 g) in toluene (50 mL) at −78° C. was slowly added 2.5M n-BuLi (2 mL). The reaction mixture was stirred for 2 h, then DMF (0.5 mL) was added. The solution was stirred for 1 h at −78° C., then warmed to −10° C. Saturated NH4Cl (10 mL) was added and the mixture was allowed to warm to room temperature. The two phases were partitioned and the organic layer dried over sodium sulfate and the solvent concentrated to dryness to afford 0.432 g of the title compound.

Workup

  1. customat −78° C.
  2. stirringThe solution was stirred for 1 h at −78° C.
  3. temperatureto warm to room temperature
  4. customThe two phases were partitioned
  5. dry with materialthe organic layer dried over sodium sulfate
  6. concentrationthe solvent concentrated to dryness

Sources & evidence

ORD record
ord-d5741d4b462644598c47a1f95df2ed83
Source dataset
uspto-grants-2009_08
Patent number
US07579353B2

Reaction notes

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