Thionyl Chloride → HCID 69106520, compound

HRID 33480Notes

Reaction equation

HRID 33480 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:22])([F:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19]O)=[N:17][CH:18]=2)=[CH:9][CH:8]=1>CN(C)C=O>[Cl:3][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([F:22])([F:21])[F:5])=[CH:8][CH:9]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21936189[5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol

Product 1

HCID 69106520HCID 69106520, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

658 mg (0.40 ml, 5.53 mmol) thionyl chloride is added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 700 mg (2.76 mmol) [5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol, stirred for 5 min. at 0° C., and at room temperature (r.t.) for 1 h. The mixture is poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with ethyl acetate. The combined organic phases were washed with water, dried (sodium sulphate), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:4) gave 170 mg (23%) of 2-Chloromethyl-5-(4-trifluoromethyl-phenyl)-pyridine as slightly pink crystals.

Workup

  1. waitat room temperature (r.t.) for 1 h
  2. additionThe mixture is poured on ice/sodium bicarbonate solution
  3. customthe organic phase separated
  4. extractionThe water phase is extracted with ethyl acetate
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (sodium sulphate)
  7. customevaporated
  8. customPurification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:4)

Sources & evidence

ORD record
ord-316b49fa985340f99c4901bf58bce526
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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