Thionyl Chloride → 2-(Chloromethyl)-3-fluoropyridine Hydrochloride

HRID 861632Notes

Reaction equation

HRID 861632 reaction equation
O[CH2:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:12])=O>ClCCl>[ClH:12].[Cl:12][CH2:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19703803(3-Fluoropyridin-2-yl)methanol

Product 1

HCID 197038622-(Chloromethyl)-3-fluoropyridine HydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-hydroxymethyl-3-fluoropyridine(3.43 g, 27 mmol) in dichloromethane (30 mL) cooled to -10° C. was added neat thionyl chloride (4.4 mL, 60 mmol) dropwise over 5 minutes. The resultant pale green solution was stirred at -10° C. for 3 hours followed by evaporation to dryness to provide 4.66 g (95%) of the titled product as an off-white crystalline solid:

Workup

  1. customfollowed by evaporation to dryness

Sources & evidence

ORD record
ord-2b26431bfb324d7eaf37255097e763c7
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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