Potassium Iodide → HCID 43231151, compound

HRID 1107522Notes

Reaction equation

HRID 1107522 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:18][C:19](=[O:21])[CH3:20]>O.CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:18][C:19](=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 805982-Bromobenzenethiol

Product 1

HCID 43231151HCID 43231151, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

20 g (105.7 mmol) of 2-bromothiophenol, 19 g (137.5 mmol) of potassium carbonate, 27.8 g (165.5 mmol) of potassium iodide, 200 ml of dimethylformamide and 14.68 g (158.6 mmol) of chloroacetone are introduced into a 500 ml three-necked flask. The mixture is stirred for 2 hours at room temperature and is then poured into 800 ml of water. Extraction is carried out with ethyl acetate (3×400 ml). The organic phases are combined, washed with a molar sodium hydroxide solution (2×400 ml), dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solution: 10% ethyl acetate in cyclohexane). 24.1 g (Yield: 93%) of (2-bromothiophenoxy)acetone are obtained (yellow oil).

Workup

  1. extractionExtraction
  2. washwashed with a molar sodium hydroxide solution (2×400 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on a silica column (elution solution: 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-ed1a687ee17949c7bb26d98064495a39
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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