Oxalyl chloride → 4-Fluorobenzoyl isocyanate

HRID 538415

Reaction equation

HRID 538415 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)[C:12](Cl)=[O:13]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:8]=[C:12]=[O:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 715724-Fluorobenzamide

Product 1

HCID 27333754-Fluorobenzoyl isocyanateYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-fluorobenzamide (1 g, 7.2 mmol) in DCM (25 mL) was added slowly oxalylchloride (0.76 mL, 8.62 mmol). The mixture was heated to 50° C. for ˜18 hr. The mixture was allowed to cool to room temperature and concentrated in vacuo to afford crude 4-fluorobenzoyl isocyanate (1.2 g). The crude material was used in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2036fb3f31d74ad28e98521a32791a68
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Linked notes

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