Pyridine → trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chloride

HRID 67820Notes

Reaction equation

HRID 67820 reaction equation
[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].N1C=CC=CC=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7]([Cl:24])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86736787trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86736786trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chlorideYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 4.1 g (0.0173 mole) of trans-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid in 40 ml of toluene at ambient temperature was added 1.7 g (0.022 mole) of pyridine, then 2.6 g (0.022 mole) of thionyl chloride in 25 ml of toluene. Upon complete addition the reaction mixture was stirred at ambient temperature for 17 hours. The reaction mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure to give 3.8 g of trans-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride. The ir spectrum was consistent with the assigned structure.

Workup

  1. additionUpon complete addition the reaction mixture
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-05f7045216b5488598b97362be470e75
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Reaction notes

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