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

HRID 33503Notes

Reaction equation

HRID 33503 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([CH3:18])[C:15]([CH2:19]O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>CN(C)C=O>[Cl:3][CH2:19][C:15]1[C:16]([CH3:18])=[N:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69106558[6-(4-Fluorophenyl)-2-methyl-3-pyridinyl]methanol

Product 1

HCID 691065843-Chloromethyl-6-(4-fluoro-phenyl)-2-methyl-pyridineYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.1 g (6.2 ml, 85 mmol) thionyl chloride is added drop by drop within 15 min. at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 9.24 g (42.5 mmol) [6-(4-Fluor-phenyl)-2-methyl-pyridin-3-yl]-methanol, and stirred for 3 h at room temperature (r.t.) The mixture is poured on ice/sodium bicarbonate solution, the organic phase separated, washed with water, dried (sodium sulphate), and evaporated. 9.78 g (97%) of the title compound were obtained.

Workup

  1. additionis poured on ice/sodium bicarbonate solution
  2. customthe organic phase separated
  3. washwashed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-173068384c7d440f83d0112e50ba7394
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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