2,6-Dibromopyridine → 4-(2-Bromopyrid-6-ylthio)butyric acid

HRID 2413134Notes

Reaction equation

HRID 2413134 reaction equation
[Na].[SH:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>CCO>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])[N:11]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 257004-Mercaptobutanoic acidHCID 5360545Sodium

Product 1

HCID 201846404-(2-Bromopyrid-6-ylthio)butyric acidYield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium (1.84 g.), EtOH (100 ml.) and 4-mercaptobutyric acid (5.28 g.) was heated to reflux and then treated with 2,6-dibromopyridine (9.5 g.), and the mixture heated under reflux for 18 hours and then evaporated to dryness. The residue was partitioned between water and ether and the aqueous phase was acidified with HOAc and extracted with ether. The ether extract was dried and evaporated to dryness to give 4-(2-bromopyrid-6-ylthio)butyric acid (9.5 g.), m.p. 72°-74°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 18 hours
  5. customevaporated to dryness
  6. customThe residue was partitioned between water and ether
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. customwas dried
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-7f36679853c948b282309ff131765c93
Source dataset
uspto-grants-1985_01
Patent number
US04496564

Reaction notes

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