Sodium methanethiolate → HCID 67004755, compound

HRID 563880Notes

Reaction equation

HRID 563880 reaction equation
Br[CH:2]([O:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:19][S-:20].[Na+]>O1CCOCC1>[CH3:19][S:20][CH:2]([O:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 85975967HCID 85975967, compound

Product 1

HCID 67004755HCID 67004755, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

t-Butyl 2-bromo-2-(3,5-dichlorophenoxy)acetate (1.0 g) was dissolved in 1,4-dioxane (3 ml), and sodium thiomethoxide (0.218 g) was added to the mixture. The resulting pale yellow suspension was stirred at ambient temperature for 5 hours and then stored for 18 hours. The solvent was evaporated, water was added and the aqueous layer was extracted twice with ethyl acetate (100 ml). The organic layers were combined, washed with brine, dried over magnesium sulphate, filtered and evaporated to give t-butyl 2-methylthio-2-(3,5-dichlorophenoxy)acetate as a pale yellow solid (0.80 g) which was used in the next step without further purification.

Workup

  1. waitstored for 18 hours
  2. customThe solvent was evaporated
  3. additionwater was added
  4. extractionthe aqueous layer was extracted twice with ethyl acetate (100 ml)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-19b28c97453645d2bd8a737233fdaa12
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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