Thionyl Chloride → 4-Cyano-3-fluorobenzoyl chloride

HRID 1773362Notes

Reaction equation

HRID 1773362 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][C:4]=1[F:12])#[N:2].O=S(Cl)[Cl:15]>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:15])=[O:8])=[CH:5][C:4]=1[F:12])#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27784684-Cyano-3-fluorobenzoic acid

Product 1

HCID 199567394-Cyano-3-fluorobenzoyl chlorideYield 99%

Procedure

A mixture of 4-cyano-3-fluoro-benzoic acid (2.0 g, 12.12 mmol) in SOCl2 (20 mL) was refluxed for 2 h, and SOCl2 was removed in vacuo to give 4-cyano-3-fluoro-benzoyl chloride (2.2 g, 99%). The crude was carried to the next step without further purification.

Workup

  1. temperaturewas refluxed for 2 h
  2. customSOCl2 was removed in vacuo

Sources & evidence

ORD record
ord-71b94d3b50a94d98bc4ea4d07b409500
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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