Tris(2-carboxyethyl)phosphine hydrochloride → 4-Bromo-2-(trifluoromethyl)benzenethiol

HRID 1367481Notes

Reaction equation

HRID 1367481 reaction equation
[Br: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.Cl.C(CCP(CCC(O)=O)CCC(O)=O)(O)=O>O1CCOCC1.O>[Br: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

5

Reactant 2

HCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 27786084-Bromo-2-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 509979974-Bromo-2-(trifluoromethyl)benzenethiolYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-bromo-2-trifluoromethyl-benzene sulfonyl chloride (9.38 g, 29 mmol) in dioxane (45 mL) and water (10 mL) was added tris-(2-carboxyethyl)phosphine hydrochloride (34.4 g, 118 mmol) and the reaction mixture was refluxed for 5 h, then cooled down, and partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane and combined organic layers were washed with water then dried over sodium sulfate and concentrated in vacuo to afford the title compound (7.00 g, 94%) as a colorless liquid. MS (EI): 254.9 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperaturecooled down
  3. custompartitioned between water and dichloromethane
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washwere washed with water
  6. dry with materialthen dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64d6ab0fe2f44efe984959b083c53b7a
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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