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

HRID 1242342Notes

Reaction equation

HRID 1242342 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]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[N:3]=1.O=S(Cl)[Cl:23]>C(Cl)Cl>[Cl:23][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935631HCID 21935631, compound

Product 1

HCID 219357213-Chloromethyl-2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.300 g (1.059 mmol) of the above prepared [2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridin-3-yl]-methanol was dissolved in 5.3 ml of CH2Cl2 and treated dropwise at 0° C. with 0.15 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° C. for 5 Min. and at RT for 30 Min. Pouring onto crashed ice/NaHCO3, twofold extraction with AcOEt, washing with water, drying over sodium sulfate and evaporation of the solvents generated 0.315 g of pure title compound as light yellow oil.

Workup

  1. customwas kept at 0° C. for 5 Min
  2. customat RT
  3. additionPouring
  4. extractionice/NaHCO3, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate and evaporation of the solvents

Sources & evidence

ORD record
ord-12f6c7c9e91844e791c89823121b062c
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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