Hydrochloric Acid → 2-Ethylthio-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

HRID 358192Notes

Reaction equation

HRID 358192 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:23]([SH:25])[CH3:24].[H-].[Na+].Cl>CN(C)C=O>[CH2:23]([S:25][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 20142103HCID 20142103, compound

Product 1

HCID 212870712-Ethylthio-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Iodo-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (0.1 mole) in dimethylformamide (500 ml) was cooled to 0°. Cuprous oxide (0.11 mole) was added, followed by ethyl mercaptan (0.1 mole). The mixture was stirred while sodium hydride (0.25 mole) was added in portions. After 15 minutes the temperature was raised to 80° for 6 hours. The mixture was cooled and poured into hydrochloric acid (2 molar). The mixture was twice extracted with ether. The ether extract was washed with water, dried (Na2SO4) and evaporated. The residue was recrystallised from ether to give 2-ethylthio-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid, with a melting point of 153°-155°.

Workup

  1. additionwas added in portions
  2. temperatureAfter 15 minutes the temperature was raised to 80° for 6 hours
  3. temperatureThe mixture was cooled
  4. extractionThe mixture was twice extracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was recrystallised from ether

Sources & evidence

ORD record
ord-1797d511ba6a413db785773efcbc307b
Source dataset
uspto-grants-1984_08
Patent number
US04465508

Reaction notes

Loading…