Sulfuryl chloride → 2-Chloro-4-(2,2,2-trifluoroethoxy)phenol

HRID 51078Notes

Reaction equation

HRID 51078 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.S(Cl)([Cl:17])(=O)=O>C(NCC(C)C)C(C)C.C1(C)C=CC=CC=1>[Cl:17][C:7]1[CH:6]=[C:5]([O:4][CH2:3][C:2]([F:12])([F:13])[F:1])[CH:10]=[CH:9][C:8]=1[OH:11]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 130853484-(2,2,2-Trifluoroethoxy)phenol

Product 1

HCID 227373642-Chloro-4-(2,2,2-trifluoroethoxy)phenolYield 106.1%

Reagents, catalysts & solvents 2

HCID 8085DiisobutylamineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a 30 ml toluene solution of 4-(2,2,2-trifluoroethoxy)phenol (1.02 g, 5.31 mmol) and diisobutylamine (0.074 ml, 0.42 mmol) was added sulfuryl chloride (0.38 ml, 4.7 mmol). This solution was heated to 70° C. for 2 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and sat. bicarb. solution. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound as a pale yellow oil 1.13 g (94%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and sat. bicarb
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel eluting with 10% AcOEt/hexanes

Sources & evidence

ORD record
ord-155ed8dcc6f14da493eeb5ee528efb71
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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