Thionyl Chloride → [Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

HRID 1726970Notes

Reaction equation

HRID 1726970 reaction equation
[CH3:1][C:2]1[C:7]([CH:8](O)[CH3:9])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1.O=S(Cl)[Cl:23]>C(Cl)Cl>[Cl:23][CH:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][CH:6]=1)[CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69035957[Rac]-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

Product 1

HCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.472 g (1.68 mmol) of the above prepared [rac]-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol was dissolved in 8 ml of CH2Cl2 and treated dropwise at 0° C. with 0.399 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° 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 yielded 0.488 g of pure title compound as light yellow oil.

Workup

  1. customwas kept at 0° 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-0f202053bb2b4f55ba947f4665d19adc
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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