Thionyl Chloride → 2-Fluoropyridine-5-carbonyl chloride

Reaction equation

[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([Cl:13])=[O:10])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 2428196-Fluoronicotinic Acid

Product 1

HCID 146236022-Fluoropyridine-5-carbonyl chloride

Conditions

Temperature: 80 °C

Procedure

In a 100-mL round-bottom flask was placed a solution of 6-fluoropyridine-3-carboxylic acid (5.0 g, 35.4 mmol) in thionyl chloride (20 mL). The resulting solution was heated at 80° C. for 2 hours and concentrated under vacuum to give the title compound as a yellow oil.

Workup

customIn a 100-mL round-bottom flask was placed
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-7ebacbd88c974eeaa7baa374f072bab9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309222B2

Reaction notes

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