Dichloromethane → 2-Bromo-1-(4-chlorophenyl)propan-1-one

HRID 1517178Notes

Reaction equation

HRID 1517178 reaction equation
ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[Br:8][CH:9]([CH3:13])[C:10](Br)=[O:11].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Br:8][CH:9]([CH3:13])[C:10]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)=[O:11]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7964ChlorobenzeneHCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-oneYield 95.5%

Conditions

Temperature
10 °C

Procedure

To 200 ml of dichloromethane are added 23.7 g (0.176 M) of aluminium chloride. The mixture is cooled to 10° C. and 10 g (0.089 M) of chlorobenzene are added dropwise. The resulting mixture is stirred for one hour at 15° C. followed by dropwise addition of 9.2 ml (0.089 M) of 2-bromopropionyl bromide. The reaction medium is then stirred for 16 hours at room temperature. The reaction medium is then poured into an ice/water mixture. The organic phase is separated out by settling, washed twice with demineralised water and then dried over sodium sulfate. After evaporating under vacuum, an oil is obtained, which crystallises to give 21 g of 2-bromo-1-(4-chlorophenyl)propan-1-one.

Workup

  1. stirringThe reaction medium is then stirred for 16 hours at room temperature
  2. customThe organic phase is separated out
  3. washwashed twice with demineralised water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating under vacuum
  6. customan oil is obtained
  7. customwhich crystallises

Sources & evidence

ORD record
ord-fc1d84f0ec9647569ece373ad4278bfa
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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