Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

HRID 2366995Notes

Reaction equation

HRID 2366995 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]>C1COCC1.CCOCC>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 117692346-Bromo-3-pyridinecarboxaldehydeYield 37.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2,5-Dibromopyridine 9.48 g (40 mmol) was dissolved in 60 mL of THF and 150 mL of anhydrous ether. After the solution was cooled to −78° C., 16 mL of n-butyllithium (2.5 M, 40 mmol) was slowly dropped through a syringe in 30 min. After being stirred at −78° C. for 30 minutes, N,N-dimethylformamide (3.5 g, 48 mmol) was added. The reaction mixture was warmed up to room temperature during two hours and then quenched by addition of 10 ml water. The mixture was extracted twice using EtOAc. The combined extracts were dried and concentrated. After flash column using 30-40% EtOAc in hexane, 2.80 g white solid was obtained (28% yield), MS: (M+H)+ 186.0, 188.0.

Workup

  1. temperatureThe reaction mixture was warmed up to room temperature during two hours
  2. customquenched by addition of 10 ml water
  3. extractionThe mixture was extracted twice using EtOAc
  4. customThe combined extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8dc5cc0073b84dfdb6588b3aa354063f
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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