Dimethyl Sulfoxide → HCID 131713482, compound

HRID 325822Notes

Reaction equation

HRID 325822 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F: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.C(=O)([O-])[O-].[K+].[K+].Br[CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].C[S:37]([CH3:39])=O>O>[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:7])=[C:39]([CH:6]=1)[S:37][CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13318225HCID 13318225, compound

Product 1

HCID 131713482HCID 131713482, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(2-Chloro-4-trifluoromethylphenoxy)-2-(methylthio)phenol (9.5 grams; 0.0296 mole), potassium carbonate (16.56 grams; 0.12 mole) ethyl 2-bromopropionate (7.79 ml; 0.06 mole) and dimethylsulfoxide (150 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer. The mixture was stirred at room temperature for a period of about 7 hours. After this time the reaction mixture poured into 600 ml of water. The resulting mixture was then extracted three times with 100 ml portions of methylene chloride. The extracts were combined and washed with water. The washed extract was then dried using a phase separator. The dried solution was stripped of solvent under aspirator pressure leaving a clear oil as the residue. The residue was chromatographed through a clay column using hexane and ethyl acetate as the eluant. Fourteen fractions were collected and fraction 12 was stripped of solvents to yield the desired product ethyl 2-[5-(2-chloro-4-trifluoromethylphenoxy)-2-methylthiophenoxy]propionate as a white crystalline solid melting at 70° to 71° C.

Workup

  1. customequipped with a mechanical stirrer
  2. extractionThe resulting mixture was then extracted three times with 100 ml portions of methylene chloride
  3. washwashed with water
  4. extractionThe washed extract
  5. customwas then dried
  6. customleaving a clear oil as the residue
  7. customThe residue was chromatographed through a clay column
  8. customFourteen fractions were collected

Sources & evidence

ORD record
ord-dde3d34b5bad447e81ff45a1033e65a0
Source dataset
uspto-grants-1984_04
Patent number
US04443248

Reaction notes

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