Thionyl Chloride → 2-Chloro-2,3,3-trifluoro-1-methylcyclobutane-1-carbonyl chloride

HRID 2372040Notes

Reaction equation

HRID 2372040 reaction equation
[CH3:1][C:2]1([C:10]([OH:12])=O)[CH2:5][C:4]([F:7])([F:6])[C:3]1([F:9])[Cl:8].S(Cl)([Cl:15])=O>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:1][C:2]1([C:10]([Cl:15])=[O:12])[CH2:5][C:4]([F:7])([F:6])[C:3]1([Cl:8])[F:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 14721525HCID 14721525, compound

Product 1

HCID 147215262-Chloro-2,3,3-trifluoro-1-methylcyclobutane-1-carbonyl chlorideYield 75.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

One drop of dimethylformamide is added to a mixture of 91.2 g (0.45 mol) of 1-methyl-2,3,3-trifluoro-2-chlorocyclobutane-1-carboxylic acid and 450 ml of chloroform. After this, 80.3 g (0.675 mol) of thionyl chloride are added dropwise at 25°-30° C. with stirring, and the stirred mixture is heated to the boil. After 6 hours the mixture is cooled, the solvent is stripped off, and the residue is subjected to fractional distillation under reduced pressure. 75 g (75% of theory) of 1-methyl-2-chloro-2,3,3-trifluoro-cyclobutane-1-carbonyl chloride are obtained in form of a liquid of boiling point 65°-70° C. at 20 mbar. ##STR60##

Workup

  1. temperaturethe stirred mixture is heated to the boil
  2. temperatureAfter 6 hours the mixture is cooled
  3. distillationthe residue is subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-7dbe3f1fcdf34f5f8fc4fc34d77d31c8
Source dataset
uspto-grants-1992_03
Patent number
US05097050

Reaction notes

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