Phosphorus oxychloride → 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

HRID 877914Notes

Reaction equation

HRID 877914 reaction equation
O=P(Cl)(Cl)[Cl:3].[I:6][C:7]1[CH:8]=[C:9]([C:14]([F:17])([F:16])[F:15])[C:10](O)=[N:11][CH:12]=1>CN(C=O)C>[Cl:3][C:10]1[C:9]([C:14]([F:17])([F:16])[F:15])=[CH:8][C:7]([I:6])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517797HCID 178517797, compound

Product 1

HCID 115005132-Chloro-5-iodo-3-(trifluoromethyl)pyridineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To an ice-cold mixture of POCl3 (1.60 mL) and DMF (1 mL) in a microwave vial, 5-iodo-3-trifluoromethyl-2-pyridinol (1 g, 3.47 mmol) is added. The vial is sealed and heated 20 min at 110° C. The reaction mixture cooled at room temperature is poured into ice cold water. The product precipitates. The precipitate is filtered, washed with cold water and dried to afford 661 mg (62%) of a light brown powder.

Workup

  1. additionis added
  2. customThe vial is sealed
  3. temperatureThe reaction mixture cooled at room temperature
  4. additionis poured into ice cold water
  5. customThe product precipitates
  6. filtrationThe precipitate is filtered
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-d80b058f45e541ff803fd438acf96caf
Source dataset
uspto-grants-2015_03
Patent number
US08987452B2

Reaction notes

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