Thionyl Chloride → 2-Fluoropyridine-3-carbonyl chloride

HRID 1802287Notes

Reaction equation

HRID 1802287 reaction equation
[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:13])=O>>[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 960892-Fluoronicotinic acid

Product 1

HCID 219595822-Fluoropyridine-3-carbonyl chlorideYield 78.8%

Procedure

A mixture of 2-fluoronicotinic acid (5.00 g, 35.4 mmol) and thionyl chloride (35 ml, 480 mmol) was refluxed for 48 hours. The thionyl chloride was distilled off at ambient pressure, the residue was distilled under high vacuum. The reaction affords 2-fluoronicotinoyl chloride (4.45 g, 78.7%) as white solid. MS: m/z=156.1 (M+H+).

Workup

  1. temperaturewas refluxed for 48 hours
  2. distillationThe thionyl chloride was distilled off at ambient pressure
  3. distillationthe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-b3b362efda1444e188613ee0120f39e9
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

Loading…