Water → 4-Fluoro-2-trifluoromethylbenzenethiol

HRID 1697554Notes

Reaction equation

HRID 1697554 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=O)=O)=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.O>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([C:12]([F:15])([F:13])[F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 27375484-Fluoro-2-(trifluoromethyl)benzenesulfonyl Chloride

Product 1

HCID 509980024-Fluoro-2-trifluoromethylbenzenethiolYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

4-Fluoro-2-(trifluoromethyl)benzenesulphonyl chloride (2.0 g) was dissolved in dioxane (12 mL) under a N2-atmosphere at ambient temperature. Water (3.0 mL) and tris-(2-carboxylethyl)phosphine hydrochloride (8.73 g) was added afterwards. The reaction mixture is stirred under reflux for 6 h. The reaction mixture is cooled to 25° C. and dissolved with water (30 mL). The product is extracted with CH2Cl2 (100 mL) several times. The combined organic layers are washed with water and dried over Na2SO4. The organic layer is filtrated and evaporated to dryness to yield 1.27 g (85%) of a colorless liquid which is used without further purification. MS (ESI): m/z=194.9 [M−H]−.

Workup

  1. temperatureunder reflux for 6 h
  2. extractionThe product is extracted with CH2Cl2 (100 mL) several times
  3. washThe combined organic layers are washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationThe organic layer is filtrated
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-70ace7d7a7c14a90af1d1ee56e3e8411
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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