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Thionyl Chloride → 2,4-Dichloro-3-cyano-5-fluorobenzoyl chloride

HRID 1976875
Notes
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Reaction equation

HRID 1976875 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[C:8]([Cl:18])=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[Cl:16])[C:10](O)=[O:11])#[N:6].[ClH:19].S(=O)=O>N1C=CC=CC=1>[C:5]([C:7]1[C:8]([Cl:18])=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[Cl:16])[C:10]([Cl:19])=[O:11])#[N:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 109005412,4-Dichloro-3-cyano-5-fluorobenzoic acidHCID 22338718Hydrogen chloride sulphur dioxide

Product 1

HCID 143001312,4-Dichloro-3-cyano-5-fluorobenzoyl chlorideYield 95.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4100 ml of thionyl chloride and 41 ml of pyridine were introduced into a stirred apparatus fitted with metering device and gas outlet leading to a scrubber via a reflux condenser, and, at 20° C., 2050 g of 3-cyano-2,4-dichloro-5-fluorobenzoic acid (99.5% strength) were introduced at the rate of hydrogen chloride/sulphur dioxide evolution. At the end of the addition, the mixture was heated to reflux until the evolution of gas ceased. The mixture was then distilled. In the boiling range from 142 to 145° C./10 mbar, 2150 g (95.7% of theory) of 3-cyano-2,4-dichloro-5-fluorobenzoyl chloride were obtained (content according to GC: 98.0%).

Workup

  1. customfitted with metering device and gas outlet
  2. customleading to a scrubber via a reflux condenser
  3. additionAt the end of the addition
  4. temperaturethe mixture was heated
  5. temperatureto reflux until the evolution of gas
  6. distillationThe mixture was then distilled

Sources & evidence

ORD record
ord-775c91f7842f4a1d84ab795883902ce7
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06229040B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes