Sodium Iodide → 2-Bromobenzene-1-carbonyl cyanide

HRID 248652Notes

Reaction equation

HRID 248652 reaction equation
[I-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7].[C:13](#[N:15])C>>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([C:13]#[N:15])=[O:7]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 235422-Bromobenzoyl chloride

Product 1

HCID 129692022-Bromobenzene-1-carbonyl cyanideYield 50%

Procedure

The reaction was carried out under Argon. Cuprous cyanide (6.52 g, 72.8 mmol) and anhydrous sodium iodide (20.25 g, 135 mmol) were stirred for 2 minutes in anhydrous acetonitrile (100 ml). The resulting solution was mixed with o-bromo benzoyl chloride (15.0 g, 68 mmol) whereupon an orange precipitate formed. The mixture was stirred for 30 minutes at room temperature, filtered and concentrated in vacuo. The residue was taken up in dichloromethane and the resulting precipitate was filtered off. Concentration of the filtrate under reduced pressure gave a yellow solid. Recrystallisation from 60°-80° C. b.p.t. petroleum ether afforded o-bromo benzoyl cyanide as yellow crystals (7.14 g, 50%), melting point 64° C.

Workup

  1. customformed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. filtrationthe resulting precipitate was filtered off
  5. customConcentration of the filtrate under reduced pressure gave a yellow solid
  6. customRecrystallisation from 60°-80° C. b.p.t

Sources & evidence

ORD record
ord-9a11406d8d2f473788db22b1f38ae61f
Source dataset
uspto-grants-1993_05
Patent number
US05210312

Reaction notes

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