Hydrochloric Acid → Ethyl 2-(3-bromopyridin-2-ylthio)-2-methylpropanoate

HRID 45777Notes

Reaction equation

HRID 45777 reaction equation
[Br:1][C:2]1[C:3]([SH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](Br)([CH3:15])[CH3:14])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C=O)C>[Br:1][C:2]1[C:3]([S:8][C:13]([CH3:15])([CH3:14])[C:12]([O:11][CH2:9][CH3:10])=[O:17])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178527856HCID 178527856, compound

Product 1

HCID 67997086Ethyl 2-(3-bromopyridin-2-ylthio)-2-methylpropanoateYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-bromopyridine-2-thiol (189 mg, 1 mmol), ethyl-2-bromoisobutyrate (390 mg, 2 mmol) and sodium carbonate (159 mg, 1.5 mmol) in DMF (2 mL) was heated to 70° C. for 1 hour. The reaction mixture was neutralized with HCl aq. 1M and extracted with ethyl acetate. The organic layer was dried over Mg2SO4, concentrated and purified by chromatography to yield ethyl 2-(3-bromopyridin-2-ylthio)-2-methylpropanoate (0.271 g, 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Mg2SO4
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-33faaedd48f7453eb4ab9c9cee59c6c7
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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