Acetic Acid → 3,5-Dibromopyridine-2-carboxylic acid

HRID 917620Notes

Reaction equation

HRID 917620 reaction equation
C([C:3]1[C:8]([Br:9])=[CH:7][C:6]([Br:10])=C[N:4]=1)#N.[C:11]([OH:14])(=[O:13])[CH3:12].S(=O)(=O)(O)O>O>[Br:10][C:6]1[C:12]([C:11]([OH:14])=[O:13])=[N:4][CH:3]=[C:8]([Br:9])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 123612023,5-Dibromopicolinonitrile

Product 1

HCID 123612423,5-Dibromopyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

2-Cyano-3,5-dibromopyridine (prepared in the above (2)) 3.27 g is added to a mixture of acetic acid 14 ml, sulfuric acid 14 ml and water 14 ml, and the mixture is refluxed at 140° C. for 4 hours. The reaction mixture is cooled and water is added thereto. The resulting precipitate is filtered and washed with water. The precipitate is dissolved in ether, washed and dried. The solvent is removed in vacuo and crystallized from a mixture of ether and hexane to give 3,5-dibromopyridine-2-carboxylic acid. mp 170-171° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water
  4. dissolutionThe precipitate is dissolved in ether
  5. washwashed
  6. customdried
  7. customThe solvent is removed in vacuo
  8. customcrystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-b6ee04370ce3413fbe72ab918aab4c03
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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