Sulfuric acid magnesium salt (1:1) → 3,5-Dichloro-4-fluorobenzonitrile

HRID 1710213Notes

Reaction equation

HRID 1710213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[F:10])[C:5]#[N:6].[F:12]C1C([N+]([O-])=O)=CC(C#N)=CC=1[N+]([O-])=O.ClCl.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[F:10])[C:5]#[N:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[F:10])[C:5]#[N:6]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24526Chlorine2×HCID 136434684-Fluoro-3,5-dinitrobenzonitrile2×HCID 136434693,5-Dichloro-4-fluorobenzonitrile

Product 2

HCID 136434693,5-Dichloro-4-fluorobenzonitrileHCID 136434703-Chloro-4,5-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
350 °C

Procedure

Preparation of 3,5-dichloro-4-fluorobenzonitrile. During a 10-hour period a solution of 216 parts of 4-fluoro-3,5-dinitrobenzonitrile (prepared as in step (a), above) in 1500 parts of carbon tetrachloride, is vaporized by passing through a tubular nickel reactor maintained at about 350° C. and the vapors passed through a second nickel tubular reactor, maintained at about 350° C., and mixed therein with a stream of chlorine at a molar ratio of Cl2 :4-fluoro-3,5-dinitrobenzonitrile of about 6.0. The exiting vapors are collected, condensed and the condensate treated with MgSO4. The desired product, 3,5-dichloro-4-fluorobenzonitrile is isolated by vacuum distillation.

Workup

  1. customby passing through a tubular nickel reactor
  2. customthe vapors passed through a second nickel tubular reactor
  3. temperaturemaintained at about 350° C.
  4. additionmixed
  5. customThe exiting vapors are collected
  6. customcondensed

Sources & evidence

ORD record
ord-6b227b2af97e4ea9a8119b1f8fb70d10
Source dataset
uspto-grants-1990_08
Patent number
US04952719

Reaction notes

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