Potassium Iodide → 4-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylbromide

HRID 2165939Notes

Reaction equation

HRID 2165939 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH:15][C:16]1[C:21]([CH2:22][CH2:23][CH3:24])=[C:20]([SH:25])[CH:19]=[CH:18][C:17]=1[C:26](=[O:28])[CH3:27]>CC(C)=O>[C:26]([C:17]1[CH:18]=[CH:19][C:20]([S:25][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[C:21]([CH2:22][CH2:23][CH3:24])[C:16]=1[OH:15])(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-one

Product 1

HCID 157123844-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylbromideYield 52.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a refluxing mixture of 1.4-dibromobutane (32.9 g), anhydrous potassium carbonate (5.25 g) and potassium iodide (1 g) in acetone (100 ml) was added dropwise a solution of 2'-hydroxy-4'-mercapto-3'-propylacetophenone (8.00 g) in acetone (20 ml) during an hour and refluxed for 2 hours. The mixture was filtered off and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography, eluting with benzene, to give the title compound (6.90 g, 52.6 %) as yellow oil.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe mixture was filtered off
  3. customthe solvent was evaporated
  4. customThe resulting residue was purified by silica gel column chromatography
  5. washeluting with benzene

Sources & evidence

ORD record
ord-6b8f82f9dd2b41a1bf65120175688d3d
Source dataset
uspto-grants-1990_07
Patent number
US04942245

Reaction notes

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