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Thionyl Chloride → 2-Fluoropyridine-3-carbonyl chloride

HRID 238523
Notes
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Reaction equation

HRID 238523 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.O=S(Cl)[Cl:13]>>[F:1][C:2]1[C:7]([C:8]([Cl:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 960892-Fluoronicotinic acid

Product 1

HCID 219595822-Fluoropyridine-3-carbonyl chloride

Procedure

2-Fluoropyridine-3-carboxylic acid (7 g, Step C) was suspended in SOCl2 (100 mL). After heating under reflux for 2 h, the mixture became homogeneous. Excess SOCl2 was removed in vacuo to afford a brown solid as desired product.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 h
  3. customExcess SOCl2 was removed in vacuo

Sources & evidence

ORD record
ord-9a43b48ccf53428fb07ec0624f068c33
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642624B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes