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

HRID 890445Notes

Reaction equation

HRID 890445 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 97.6%

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 5 e]) 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 with anhydrous sodium sulfate. After evaporation, 27.9 g (97.6%) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine were obtained as a light brown solid.

Workup

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

Sources & evidence

ORD record
ord-6ea109a1aafa441ebc495c43ca4b1a39
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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