Potassium Hydroxide → HCID 54525745, compound

HRID 2227515Notes

Reaction equation

HRID 2227515 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C(O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 660494-BromothiophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 54525745HCID 54525745, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.36 g of potassium hydroxide was dissolved in 38 ml ethanol by heating, allowed to cool, mixed with 3.8 g of 4-bromobenzenethiol, further with 3.8 g of silica gel and 2.96 ml of t-butyl bromoacetate, followed by stirring at room temperature for 4 hours. Silica gel was filtered off and the filtrate was concentrated and purified via column chromatography on silica gel (ethyl acetate:hexane=1:20) to give t-butyl [(4-bromophenyl)thio]acetate (5.98 g, 98.6%).

Workup

  1. temperatureby heating
  2. temperatureto cool
  3. filtrationSilica gel was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified via column chromatography on silica gel (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-0a5852529313490c8be2c5b2cc4ce393
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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