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

HRID 1242288Notes

Reaction equation

HRID 1242288 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.O=S(Cl)[Cl:22]>C(Cl)Cl>[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)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.875 g (3.27 mmol) of the above prepared [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol was dissolved in 16 ml of CH2Cl2 and treated dropwise at 0° C. with 0.48 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 afforded 0.875 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-c68583a8e2ba4eb3bc58ba6cbbf183d9
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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