Sodium Cyanide → 3-Bromo-4-fluorobenzoyl cyanide

HRID 1702634

Reaction equation

HRID 1702634 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8](F)=[O:9]>>[F:14][C:13]1[CH:12]=[CH:11][C:7]([C:8]([C:1]#[N:2])=[O:9])=[CH:6][C:5]=1[Br:4]

Participants

3

Conditions

Temperature
100 °C

Procedure

177 g (3.6 moles) of sodium cyanide and 663 g (3 moles) of 3-bromo-4-fluorobenzoyl fluoride were together initially introduced into the reaction vessel and were heated. At about 80° C., an exothermic reaction started, which had to be restrained somewhat by slight cooling. The temperature was allowed to rise to 100° C. and the mixture was stirred at 100° C. for 1 hour. The exothermic reaction continued for about 10 minutes, and additional heat had then to be supplied to the mixture. The mixture was then cooled and the salts were filtered off and destroyed in saturated iron sulphate solution and the filtrate was distilled on a column. 507 g (74% of theory) of a colorless oil with a boiling point of 126° C./20 mm Hg were thus obtained.

Workup

  1. temperaturewere heated
  2. customAt about 80° C., an exothermic reaction
  3. customto rise to 100° C.
  4. customThe exothermic reaction
  5. waitcontinued for about 10 minutes
  6. temperatureadditional heat
  7. temperatureThe mixture was then cooled
  8. filtrationthe salts were filtered off
  9. customdestroyed in saturated iron sulphate solution
  10. distillationthe filtrate was distilled on a column
  11. custom507 g (74% of theory) of a colorless oil with a boiling point of 126° C./20 mm Hg were thus obtained

Sources & evidence

ORD record
ord-7229fbf9660844ddba4273664289dd54
Source dataset
uspto-grants-1982_09
Patent number
US04348538

Linked notes

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