O-Xylene → 118559-21-0

HRID 2273333Notes

Reaction equation

HRID 2273333 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[F:9][C:10]([F:18])([F:17])[C:11]([F:16])([F:15])C([O-])=O.[Na+].C1(C)C(C)=CC=CC=1.CN1CCCC1=O>[Cu]I.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]([F:16])([F:15])[C:10]([F:18])([F:17])[F:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 13387N-methyl-2-pyrrolidoneHCID 2733305Sodium pentafluoropropionateHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 14111645118559-21-0

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-5-iodopyridine (20.0 g), sodium pentafluoropropionate (77.8 g), copper (I) iodide (31.8 g), xylene (84 ml) and N-methylpyrrolidone (84 ml) was heated to 160° C., and stirred while heating under reflux 6 hours. The reaction mixture was cooled to room temperature, and water was poured thereto. Then, the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 2-chloro-5-pentafluoroethyl pyridine.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux 6 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThen, the mixture was extracted with methyl-tert-butyl ether
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7d4386468a94edaa71d06089df1b9df
Source dataset
uspto-grants-2015_09
Patent number
US09120823B2

Reaction notes

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