Thionyl Chloride → HCID 64950694, compound

HRID 2401705Notes

Reaction equation

HRID 2401705 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.S(Cl)([Cl:12])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:12][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 49760376(3-Fluoropyridin-4-yl)methanol

Product 1

HCID 64950694HCID 64950694, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1.12 g of (3-fluoropyridin-4-yl)methanol and 5 ml of chloroform was added dropwise 1.26 g of thionyl chloride at room temperature, and the mixture was stirred at room temperature for 1.3 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, and the mixture was extracted twice with chloroform. The organic layers were combined and washed with saturated brine and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.22 g of 4-chloromethyl-3-fluoropyridine.

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c690a1a483c44e2990b31a6423d9080
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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