Ethyl Acetate → 4-(Trifluoromethoxy)thiophenol

HRID 356844Notes

Reaction equation

HRID 356844 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=O)=O)=[CH:6][CH:5]=1.C(OCC)(=O)C>S(=O)(=O)(O)O.O.[Zn]>[F:15][C:2]([F:1])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([SH:10])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chloride

Product 1

HCID 27773604-(Trifluoromethoxy)thiophenolYield 47%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Zinc powder (3.1 g) was added to a suspension of p-trifluoromethoxybenzenesulfonyl chloride (1.36 ml) in concentrated sulfuric acid (3.4 ml) and water (20 ml), and the suspension was stirred at 0° C. for 18 hours and heated under reflux for 6 hours. The mixture was added with ethyl acetate, washed with water, saturated aqueous solution of sodium hydrogen carbonate, and saturated brine, and then concentrated under reduced pressure to give p-trifluoromethoxybenzenethiol (0.73 g, 47%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. washwashed with water, saturated aqueous solution of sodium hydrogen carbonate, and saturated brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-616c6918ac164c8091b43e3d2bfd5800
Source dataset
uspto-grants-1998_11
Patent number
US05840716

Reaction notes

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