(4-Bromobutoxy)benzene → HCID 21850250, compound

HRID 618084Notes

Reaction equation

HRID 618084 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CS(C)=O>[C:13]([S:15][CH2:11][CH2:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:16])[CH3:14]

Participants

4

Reactant 2

HCID 70986(4-Bromobutoxy)benzeneHCID 23670855Potassium ethanethioate

Product 1

HCID 21850250HCID 21850250, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Phenoxybutyl bromide (5.73 g) was dissolved in dimethyl sulfoxide, and potassium thioacetate (10.71 g) was added thereto, followed by stirring at room temperature for 18 hours. The reaction solution was subjected to partitioning between ethyl acetate and water, and the organic layer was successively washed with water and a satureted saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1-acetylthio-4-phenoxybutane (Compound XIX-1, 5.53 g).

Workup

  1. customto partitioning between ethyl acetate and water
  2. washthe organic layer was successively washed with water
  3. dry with materiala satureted saline, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-318940248bda4ddb92a7924b53c6a332
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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