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

HRID 483728Notes

Reaction equation

HRID 483728 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-c0ff0382f1d7483287c5d70a2c3abb91
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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