Thionyl Chloride → 2-(Chloromethyl)-5-fluoropyridine hydrochloride

HRID 79475Notes

Reaction equation

HRID 79475 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 24729312(5-Fluoropyridin-2-yl)methanol

Product 1

HCID 574316752-(Chloromethyl)-5-fluoropyridine hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-fluoropyridin-2-yl)methanol (10.6 g, 83.39 mmol) in DCM (166 mL) was added thionyl chloride (12.17 mL, 166.8 mmol) dropwise. The mixture was allowed to stir at ambient temperature for 18 hours. The mixture was concentrated under reduced pressure to afford 2-(chloromethyl)-5-fluoropyridine hydrochloride (11.8 g, 78% yield) as white solids.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce4d80580a8c4e79b45a0e6077192d69
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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