Bromine → 4-Chlorobenzonitrile

HRID 1073341Notes

Reaction equation

HRID 1073341 reaction equation
[Cl:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH:3]=1.BrBr>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408Bromine4×HCID 15106095HCID 15106095, compound2×

Product 1

HCID 121634-Chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a 25 ml three-necked flask equipped with an equal pressure additional funnel, a dry-ice condenser with a gas outlet and a stopper, is charged 14.2 g (0.1 mole) of 1-chloro-4-cyanocyclo-hex-1-ene (I) and 3 g of chlorobenzene The mixture is heated to 90°-100° C. with stirring. Bromine, 32 g (0.2 mole), is added dropwise, sub-surface. The reddish-brown color dissipates quickly and a gas evolution occurs. When approximately 24 g of bromine has been added, the pot temperature is raised to 120°-130° C. The remaining bromine is added in the same fashion. The pot temperature may then be raised to 150°-160° C. for 2-4 hours. During this period, an additional amount of bromine, such as about 1-2 g, may be added to complete the conversion of (I). A good yield of 4-chlorobenzonitrile will be obtained by the fractional distillation of the mixture.

Workup

  1. customTo a 25 ml three-necked flask equipped with an equal pressure additional funnel, a dry-ice condenser with a gas outlet
  2. temperatureis heated to 90°-100° C.
  3. temperaturethe pot temperature is raised to 120°-130° C
  4. temperatureThe pot temperature may then be raised to 150°-160° C. for 2-4 hours
  5. waitDuring this period

Sources & evidence

ORD record
ord-eb1a253482774f5ea7a545525d0f8916
Source dataset
uspto-grants-1990_11
Patent number
US04968830

Reaction notes

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