Tetrahydrofuran → Ethylthioethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate

HRID 1156216Notes

Reaction equation

HRID 1156216 reaction equation
[CH2:1]([S:3][CH:4](O)[CH3:5])[CH3:2].C(N(CC)CC)C.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:16]=1[C:17](Cl)=[O:18].[O:36]1CCCC1>>[CH2:1]([S:3][CH2:4][CH2:5][O:18][C:17](=[O:36])[C:16]1[CH:20]=[C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][C:26]=2[Cl:35])[CH:22]=[CH:23][C:15]=1[Cl:14])[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 127996322-Chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl chlorideHCID 19024902Ethylthioethanol

Product 1

HCID 12799646Ethylthioethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoateYield 53%

Procedure

In 20 ml tetrahydrofuran were dissolved 0.8 g (0.0075 mol) of ethyl thioethanol and 0.8 g (0.0079 mol) of triethylamine, and while heating to 60°-80° C., 1.6 g (0.0043 mol) of 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride was added. After 5-hour stirring, the resulting mixture was cooled, freed of the solvent under reduced pressure, and extracted with benzene. The extract was washed with a dilute aqueous solution of caustic soda and then with dilute hydrochloric acid, and dehydrated with sodiumsulfate. By concentration, 1.0 g (0.0023 mol) of the intended product was obtained as an oily substance; yield 53.0%, nD23 1.5500.

Workup

  1. temperaturewhile heating to 60°-80° C.
  2. temperaturethe resulting mixture was cooled
  3. extractionextracted with benzene
  4. washThe extract was washed with a dilute aqueous solution of caustic soda
  5. concentrationBy concentration

Sources & evidence

ORD record
ord-1050a243f08c4fdc88ebd265f0040270
Source dataset
uspto-grants-1982_06
Patent number
US04334914

Reaction notes

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