Dimethyl Sulfoxide → Ethyl-2-[5-(2-bromo-4-nitrophenoxy)-2-methylthiophenoxy]propionate

HRID 325824Notes

Reaction equation

HRID 325824 reaction equation
[Br:1][C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8](SC)=[C:9](O)[CH:10]=1.Br[CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C[S:30]([CH3:32])=O.O>CCCCCC.C(OCC)(=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH:22]([S:30][C:32]1[CH:6]=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:2]=2[Br:1])[CH:10]=[CH:9][C:8]=1[CH3:7])[CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 79040Ethyl 2-bromopropionateHCID 204628205-(2-Bromo-4-nitrophenoxy)-2-(methylthio)phenol

Product 1

HCID 131713483Ethyl-2-[5-(2-bromo-4-nitrophenoxy)-2-methylthiophenoxy]propionate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-(2-Bromo-4-nitrophenoxy)-2-(methylthio)phenol (0.05 mole) potassium carbonate (0.2 mole), ethyl 2-bromopropionate (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 thereafter 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 mixtures as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product ethyl-2-[5-(2-bromo-4-nitrophenoxy)-2-methylthiophenoxy]propionate as the residue.

Workup

  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. customdried
  5. customto leave a residue
  6. additionThe fractions containing the product

Sources & evidence

ORD record
ord-43673f553b02436cab2f7d7d0160525b
Source dataset
uspto-grants-1984_04
Patent number
US04443248

Reaction notes

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