Chlorine → HCID 11745112, compound

HRID 2260844Notes

Reaction equation

HRID 2260844 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+]([O-])=O)[C:3]=1[C:4]#[N:5].[Cl-:14].[Ca+2].[Cl-].ClCl>>[Cl:14][C:6]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 24526ChlorineHCID 5284359Calcium ChlorideHCID 11030483HCID 11030483, compound

Product 1

HCID 11745112HCID 11745112, compoundYield 987.8%

Conditions

Temperature
190 °C

Procedure

24.8 g (0.135 mol) of 2,3-difluoro-6-nitrobenzonitrile and 1 g of anhydrous calcium chloride are placed in a 50 ml flask with a finely drawn-out gas inlet tube, and heated to 190° C. Chlorine is introduced at this temperature with a throughput of 2-3 l/h so that a uniform production of nitrous gases occurs. After a reaction time of 12 h, the starting material has been substantially converted (<10% residual content of nitro compound). The remaining nitrous gases are purged with air and the residue is distilled off under vacuum over a short Vigreux column to give 15.5 g (89 mmol, 66%) of 2-chloro-5,6-difluorobenzonitrile as a light yellowish, oily liquid boiling at 70°-75° C./3 Torr (purity (GC)>95%).

Workup

  1. customAfter a reaction time of 12 h
  2. customThe remaining nitrous gases are purged with air
  3. distillationthe residue is distilled off under vacuum over a short Vigreux column

Sources & evidence

ORD record
ord-d5e609649a464154a77c5b938859f018
Source dataset
uspto-grants-1995_12
Patent number
US05478963

Reaction notes

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