Hydrochloric Acid → p-Bromopropiophenone

HRID 1755618Notes

Reaction equation

HRID 1755618 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(=S)=S>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66312p-BromopropiophenoneYield 78.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

294 g of aluminium chloride was added to 1000 ml of carbon disulfide and stirred. The reaction solution was cooled to 0° C. or lower, and 166 g of propionyl chloride was dropwise added thereto. Next, 283 g of bromobenzene was dropwise added thereto. Then, the whole was stirred for one hour at room temperature. After reaction, the reaction solution was poured into a mixture of 300 ml of concentrated hydrochloric acid and 600 g of ice. This was extracted with chloroform and washed three times with water, and chloroform was removed by distillation. By distillation under reduced pressure (b.p. 100° to 105° C./2 mmHg), 301 g of 1-bromo-4-propionylbenzene was obtained.

Workup

  1. stirringThen, the whole was stirred for one hour at room temperature
  2. customAfter reaction
  3. extractionThis was extracted with chloroform
  4. washwashed three times with water, and chloroform
  5. customwas removed by distillation
  6. distillationBy distillation under reduced pressure (b.p. 100° to 105° C./2 mmHg)

Sources & evidence

ORD record
ord-4a2aabcc991f4765b6862350104f1629
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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