Pyridine → 1,1,1,3,3-Pentafluoro-2,3-dichloro-2-(4-ethoxyphenyl)propane

HRID 1614447Notes

Reaction equation

HRID 1614447 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)(O)[C:4]([F:7])([F:6])[Cl:5].S(Cl)([Cl:22])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:19])([F:18])[C:3]([Cl:22])([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)[C:4]([F:7])([F:6])[Cl:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 138807621,1,1,3,3-Pentafluoro-2-(4-ethoxyphenyl)-3-chloropropan-2-ol

Product 1

HCID 145170441,1,1,3,3-Pentafluoro-2,3-dichloro-2-(4-ethoxyphenyl)propane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1,1,1,3,3-pentafluoro-2-(4-ethoxyphenyl)-3-chloropropan-2-ol (28 g), thionyl chloride (45 cm3) and pyridine (3 cm3) was heated at the reflux temperature for 4 hours, diluted with toluene and the volatile components removed by evaporation under reduced pressure. The residual oil was dissolved in chloroform, washed with water and dried over anhydrous magnesium sulphate. Removal of the solvent by evaporation under reduced pressure yielded 1,1,1,3,3-pentafluoro-2,3-dichloro-2-(4-ethoxyphenyl)propane (29.5 g) as a residual oil.

Workup

  1. temperaturewas heated at the reflux temperature for 4 hours
  2. customthe volatile components removed by evaporation under reduced pressure
  3. dissolutionThe residual oil was dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customRemoval of the solvent
  7. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-56e1d4bd39914feb89b5d66af677cbeb
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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