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

HRID 1242347Notes

Reaction equation

HRID 1242347 reaction equation
[CH:1]1([C:4]2[C:9]([CH2:10]O)=[CH:8][CH:7]=[C:6]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.O=S(Cl)[Cl:24]>C(Cl)Cl>[Cl:24][CH2:10][C:9]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935842HCID 21935842, compound

Product 1

HCID 219359313-Chloromethyl-2-cyclopropyl-6-(4-trifluoromethyl-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.127 g (0.433 mmol) of the above prepared [2-cyclopropyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol was dissolved in 2.0 ml of CH2Cl2 and treated at 0° C. with 0.063 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° C. for 5 Min. and at RT for 60 Min. Pouring onto crashed ice/NaHCO3, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents afforded 0.137 g of pure title compound as off-white solid.

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 and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-6ef3057b621747d1adfe7da8b332457d
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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