1-Bromo-3-methylbutane → [4-(3-Methyl-butoxy)phenylsulfanyl]-acetic acid ethyl ester

HRID 991121Notes

Reaction equation

HRID 991121 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 3742252Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetate

Product 1

HCID 11055129[4-(3-Methyl-butoxy)phenylsulfanyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To stirred solution of (4-Hydroxy-phenylsulfanyl)-acetic acid ethyl ester (2.12 g, 10 mmol), K2CO3 (anhydrous, 10 g) and 1-bromo-3-methyl butane (3 g, excess) was added in boiling acetone. The reaction mixture was refluxed for 24 hrs and cooled to room temperature. The reaction mixture was filtered and concentrated. The residue obtained was extracted with chloroform; washed well with water and concentrated. The crude product obtained was taken to next step with out purification. Yield 2.7 g (94%); (M+H)+283.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 24 hrs
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. extractionwas extracted with chloroform
  7. washwashed well with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0573e5f28aff418394f36c6a794143a6
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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