Toluene → 2-Bromo-1-(4-(2-methylpropyl)phenyl)ethan-1-one

HRID 749225

Reaction equation

HRID 749225 reaction equation
[Br:1]Br.[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5].C1(C)C=CC=CC=1>C(O)C>[Br:1][CH2:14][C:13]([C:10]1[CH:9]=[CH:8][C:7]([CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:12][CH:11]=1)=[O:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24408BromineHCID 932144'-Isobutylacetophenone

Product 1

HCID 136563372-Bromo-1-(4-(2-methylpropyl)phenyl)ethan-1-oneYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Bromine (1.25 ml; 25 mmol) is added dropwise to a solution of 4′-isobutylacetophenone (3.52 g; 20 mmol) in 60 ml of ethanol cooled down to approximately 5° C. After stirring the reaction mixture for 30 minutes at this temperature, stirring is continued for one hour at ambient temperature. The reaction medium, to which small portions of toluene are added, is concentrated to dryness. After purification on a silica column (eluent: ethyl-heptane acetate: 5-95), a colourless oil is obtained with a yield of 57%.

Workup

  1. stirringstirring
  2. waitis continued for one hour at ambient temperature
  3. concentrationis concentrated to dryness
  4. customAfter purification on a silica column (eluent: ethyl-heptane acetate: 5-95)
  5. customa colourless oil is obtained with a yield of 57%

Sources & evidence

ORD record
ord-37cffd1cac174c97ae12e2ea559231b3
Source dataset
uspto-grants-2008_07
Patent number
US07402602B2

Linked notes

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