Thionyl Chloride → 3-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

HRID 1726982Notes

Reaction equation

HRID 1726982 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:3]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Product 1

HCID 219357513-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (26.7 g; 100 mmol) (example 1I]) in dichloromethane (100 ml) was added at 0° C. 10.9 ml (150 mmol) of thionyl chloride within 0.5 hours. Stirring was continued at ambient temperature for 1 hour. Afterwards, ice water was added and the mixture was stirred vigorously. Then, the layers were separated, the aqueous phase was extracted with 100 ml of dichloromethane. The combined organic phases were washed with water, aqueous sodium hydrogen carbonate, brine, and dried over anhydrous sodium sulfate. After evaporation, 27.9 g of the title compound was obtained as light brown solid.

Workup

  1. additionwas added at 0° C
  2. stirringthe mixture was stirred vigorously
  3. customThen, the layers were separated
  4. extractionthe aqueous phase was extracted with 100 ml of dichloromethane
  5. washThe combined organic phases were washed with water, aqueous sodium hydrogen carbonate, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporation

Sources & evidence

ORD record
ord-0b340616154f4de5b5dc9cc45c5deed1
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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