3-Fluorobenzoyl chloride → 3-Fluorobenzoyl isothiocyanate

HRID 518641Notes

Reaction equation

HRID 518641 reaction equation
[S-:1][C:2]#[N:3].[K+].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](Cl)=[O:10]>CC(C)=O>[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([N:3]=[C:2]=[S:1])=[O:10]

Participants

4

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 149841723-Fluorobenzoyl isothiocyanateYield 37.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

Potassium thiocyanate (11.03 g, 114 mmol) was suspended in acetone (63.1 mL) and heated to 40° C. under nitrogen atmosphere. To this was added 3-fluorobenzoyl chloride (11.35 mL, 95 mmol), and the resulting mixture was stirred at 50° C. for 6 hours. The heterogeneous mixture was filtered, and the solid was further washed with acetone. The filtrate was concentrated and purified by silica gel chromatography (10% EtOAc/Hexanes as the eluent) to afford 3-fluorobenzoyl isothiocyanate (6.5 g, 37.9% yield) as a light orange oil.

Workup

  1. filtrationThe heterogeneous mixture was filtered
  2. washthe solid was further washed with acetone
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography (10% EtOAc/Hexanes as the eluent)

Sources & evidence

ORD record
ord-251e2acabe6c440c90124ed683697d72
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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