Thionyl Chloride → 5-Chloromethyl-2-(4-trifluoromethoxy-phenyl)-pyridine

HRID 890453Notes

Reaction equation

HRID 890453 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.O=S(Cl)[Cl:22]>C(Cl)Cl>[Cl:22][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:19])([F:18])[F:1])=[CH:5][CH:6]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935933{6-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}methanol

Product 1

HCID 219356725-Chloromethyl-2-(4-trifluoromethoxy-phenyl)-pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[6-(4-Trifluoromethoxy-phenyl)-pyridin-3-yl]-methanol (0.40 g, 1.49 mmol) was dissolved in CH2Cl2 (7.2 ml) and treated dropwise at 0° C. with SOCl2 (0.22 ml, 2 eq.). 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 produced 0.419 g (1.46 mmol, 98%) of the title compound as off-white solid of mp. 34–36° C.

Workup

  1. additionPouring
  2. extractionice/NaHCO3, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7eda09a011c34d81afef9d728426ff14
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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