Sodium Carbonate → 2-Bromo-4-pyridinecarboxaldehyde

HRID 1110972Notes

Reaction equation

HRID 1110972 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.BrN1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 27629912-Bromo-4-pyridinecarboxaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 21.0 g of 2-bromo-4-pyridinemethanol, 32.3 g of N-bromosuccinimide and 23.1 g of anhydrous sodium carbonate was suspended in 600 ml of benzene, and heated under reflux (bath temperature 110° to 120° C.) for 4 hours. The mixture was cooled over an ice bath, and a saturated aqueous solution of sodium hydrogen carbonate was added to adjust its pH to 9 to 10. The insoluble matter was removed by filtration (by washing with ethyl acetate). The organic layer was separated, washed with a 10% aqueous solution of sodium thiosulfate and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was evaporated to give 18.2 g (yield 88%) of 2-bromo-4-pyridinecarboxaldehyde.

Workup

  1. temperatureheated
  2. temperatureunder reflux (bath temperature 110° to 120° C.) for 4 hours
  3. temperatureThe mixture was cooled over an ice bath
  4. customThe insoluble matter was removed by filtration (by washing with ethyl acetate)
  5. customThe organic layer was separated
  6. washwashed with a 10% aqueous solution of sodium thiosulfate
  7. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-957d14b0588f49308482356a06e210d3
Source dataset
uspto-grants-1990_12
Patent number
US04977267

Reaction notes

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