4-Fluorobenzoyl chloride → 4-Fluorobenzoyl isothiocyanate

HRID 1740845Notes

Reaction equation

HRID 1740845 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[S-:11][C:12]#[N:13].[K+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]=[C:12]=[S:11])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 2490894-Fluorobenzoyl isothiocyanateYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture o 4-fluorobenzoyl chloride (50 g), potassium thiocyanate (36.7 g) and anhydrous toluene (100 ml) is refluxed for six hours. After cooling, the reaction mixture is filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by distillation under reduced pressure to give 4-fluorobenzoyl isothiocyanate (55 g), b.p. 92° C/3 mmHg.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. distillationThe residue is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-0c7957a0437d40a1ae838bbe66778a0b
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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