Thionyl Chloride → 3-(Chloromethyl)-5-fluoropyridine

HRID 2200628Notes

Reaction equation

HRID 2200628 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1524495-Fluoro-3-pyridinemethanol

Product 1

HCID 216984253-(Chloromethyl)-5-fluoropyridineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-fluoropyridin-3-yl)methanol (0.19 g, 1.50 mmol) in DCM (5 mL) was added thionyl chloride (0.19 ml, 2.6 mmol) at 0° C. The reaction was stirred at room temperature for 2 h. The reaction was concentrated and the residue was dried in vacuo to yield 3-(chloromethyl)-5-fluoropyridine (166 mg) which was used without characterization.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-f37fbb0c226c4c0a873a7e1eb170bac8
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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