Potassium Hydroxide → HCID 10640226, compound

HRID 381260Notes

Reaction equation

HRID 381260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[K+].Br[C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 660494-BromothiophenolHCID 90290tert-Butyl 2-bromo-2-methylpropionate

Product 1

HCID 10640226HCID 10640226, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-bromothiophenol (100 g; 0.53 mole) and potassium hydroxide (29.5 g; 0.53 mole) in ethanol (1000 mL) was stirred until all material had dissolved. t-Butyl 2-bromoisobutyrate (117.6 g; 0.53 mole) was added dropwise over 30 min, keeping the temperature below 55° C. The resulting mixture was heated at reflux for 1 h, then cooled to 23° C. The precipitate (KBr) was removed by filtration and the solvent evaporated. The residue was partitioned between water (1000 mL) and methylene chloride (500 mL) and the organic layer was separated, dried (Na2SO4) and evaporated to afford a white solid. Crystallization from hexane gave a white solid (119.85 g; 68%).

Workup

  1. dissolutionhad dissolved
  2. customthe temperature below 55° C
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 1 h
  5. customThe precipitate (KBr) was removed by filtration
  6. customthe solvent evaporated
  7. customThe residue was partitioned between water (1000 mL) and methylene chloride (500 mL)
  8. customthe organic layer was separated
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customto afford a white solid
  12. customCrystallization from hexane
  13. customgave a white solid (119.85 g; 68%)

Sources & evidence

ORD record
ord-61fe1e5c11ca47b280422eb73843765b
Source dataset
uspto-grants-2001_10
Patent number
US06306854B1

Reaction notes

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