2,6-Dibromopyridine → HCID 20184640, compound

HRID 2309712Notes

Reaction equation

HRID 2309712 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 20184640HCID 20184640, compoundYield 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-95e7295e99c244fc9074ea581bbcbb10
Source dataset
uspto-grants-1987_09
Patent number
US04696933

Reaction notes

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