Bromine → 4-Chlorobenzoyl chloride

HRID 1073342Notes

Reaction equation

HRID 1073342 reaction equation
[Cl:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]([Cl:10])=[O:9])[CH2:4][CH:3]=1.BrBr>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([Cl:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24408Bromine4×HCID 21660597HCID 21660597, compound2×

Product 1

HCID 85014-Chlorobenzoyl chloride

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 17.9 g (0.1 mole) of 1-chloro-4-chloroformyl cyclohex-1-ene (I). The solution is heated to 90°-100° C. with stirring, using a magnetic stirring bar. Bromine, 32 g (0.2 mole), is added dropwise, sub-surface. The color dissipates quickly and a gas evolution occurs. When about 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. fro 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-chlorobenzoyl chloride 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. temperatureThe solution is 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. fro 2-4 hours
  5. waitDuring this period

Sources & evidence

ORD record
ord-2e8432481d6f43a0897a22debfd15c72
Source dataset
uspto-grants-1990_11
Patent number
US04968830

Reaction notes

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