Dimethyl Sulfoxide → Methyl 2-[5-(4-bromophenoxy)-2-methylthiophenoxy]acetate

HRID 325833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325833
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10](SC)=[C:11](O)[CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C[S:31]([CH3:33])=O>CCCCCC.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:9])=[C:33]([CH:8]=2)[S:31][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 204628445-(4-Bromophenoxy) 2-(methylthio)phenol

Produkt 1

HCID 131713487Methyl 2-[5-(4-bromophenoxy)-2-methylthiophenoxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

5-(4-Bromophenoxy)-2-(methylthio)phenol (0.05 mole), potassium carbonate (0.2 mole), methyl 2-bromoacetate (0.08 mole) and dimethylsulfoxide (200 ml) are charged into a 500 ml glass reaction flask equipped with a mechanical stirrer. The reaction mixture is stirred at room temperature for a period of about 8 hours. After this time the mixture is poured into 500 ml of water. The resulting mixture is extracted three times with 100 ml portions of methylene chloride. The extracts are then combined, washed with water and therafter dried. The dried solution is then stripped of solvent under reduced pressure to leave a residue. The residue is subjected to chromatography using a clay column and hexane/ethyl acetate mixture as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product methyl 2-[5-(4-bromophenoxy)-2-methylthiophenoxy]acetate as the residue.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. extractionThe resulting mixture is extracted three times with 100 ml portions of methylene chloride
  3. washwashed with water
  4. customtherafter dried
  5. customto leave a residue
  6. additionThe fractions containing the product

Quellen und Nachweise

ORD-Eintrag
ord-6a57ba028c5742419d27f2856c058092
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04443248

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