Water → 4-Fluoro-2-trifluoromethylbenzenethiol

HRID 1697620Notes

Reaction equation

HRID 1697620 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 g) was dissolved in 1,4-dioxane (12 mL) and water (3 mL) under a nitrogen atmosphere. Tris-(2-carboxylethyl)phosphine hydrochloride (8.73 g) was added and the mixture was stirred under reflux for 6 h. The reaction mixture was cooled to 25° C. and water (20 mL) was added. The product was extracted 3 times with CH2Cl2 (20 mL). The combined organic layers were dried over Na2SO4 filtrated and evaporated to dryness to yield the title compound (1.27 g, 85%) as a colorless liquid. MS (ESI): m/z=194.9 [M−H]−.

Workup

  1. temperatureunder reflux for 6 h
  2. extractionThe product was extracted 3 times with CH2Cl2 (20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltrated
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-726dc90012354925a2eb9970cd71a86d
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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