Thionyl Chloride → (5-Chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone

HRID 556274Notes

Reaction equation

HRID 556274 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH2:16]O)[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>C(#N)C>[Cl:20][CH2:16][C:14]1[CH:15]=[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:9])[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59200200(4-Fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone

Product 1

HCID 59200177(5-Chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanoneYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4-fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone (1I) (410 mg, 1.8 mmol) in 25 mL of acetonitrile at 0° C., is added thionyl chloride (0.65 mL, 8.9 mmol) drop wise. After being stirred at room temperature for 2 hours, the reaction mixture is concentrated to remove most of thionyl chloride and acetonitrile. The residue is dissolved in 30 mL of CH2Cl2 and basified by saturated sodium bicarbonate to PH˜8.0. The organic layer is dried over sodium sulfate and concentrated to give (5-chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone (1J) (390 mg, yield 87%) as light yellow waxy solid. MS (ESI) m/e 250 (M+H+).

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customto remove most of thionyl chloride and acetonitrile
  3. dissolutionThe residue is dissolved in 30 mL of CH2Cl2
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4596917d2d1435cb96c126b5770ba90
Source dataset
uspto-grants-2011_11
Patent number
US08058272B2

Reaction notes

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