Hydrochloric Acid → 2,6-Dibromo-3-pyridinecarboxylic acid

HRID 1512976Notes

Reaction equation

HRID 1512976 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([Br:10])[N:3]=1.P([O-])(O)(O)=[O:12].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O>[Br:1][C:2]1[N:3]=[C:4]([Br:10])[CH:5]=[CH:6][C:7]=1[C:8]([OH:12])=[O:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 122593842,6-Dibromopyridine-3-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 122593872,6-Dibromo-3-pyridinecarboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2,6-dibromo-3-formylpyridine (0.3 g) in tert-butanol (12 mL)-water (1 mL) were added sodium dihydrogen phosphate (0.14 g), 2-methyl-2-butene (0.32 g) and a solution of sodium chlorite (0.36 g) in water (2 mL) successively at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was poured into water. The mixture was acidified by adding 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.28 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb873ee1f03747e2a1067c41fa17e7bf
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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