3'-Bromoacetophenone → 2-Bromo-1-(3-bromophenyl)ethan-1-one

HRID 45631

Reaction equation

HRID 45631 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Br:11]Br>C(O)(=O)C>[Br:11][CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 165023'-BromoacetophenoneHCID 24408Bromine

Product 1

HCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed a solution of 1-(3-bromophenyl)ethanone (40 g, 202.02 mmol, 1.00 equiv) in acetic acid (200 mL). This was followed by the addition of a solution of Br2 (32 g, 200.00 mmol) in acetic acid (50 mL) dropwise with stirring at 60° C. The resulting solution was stirred for 3 h at 60° C. in an oil bath. The resulting mixture was concentrated under vacuum. The crude product was re-crystallized from petroleum ether:ethyl acetate in the ratio of 8:1. This resulted in 24 g (43%) of 2-bromo-1-(3-bromophenyl)ethanone as a yellow solid.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 3 h at 60° C. in an oil bath
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThe crude product was re-crystallized from petroleum ether
  5. customThis resulted in 24 g (43%) of 2-bromo-1-(3-bromophenyl)ethanone as a yellow solid

Sources & evidence

ORD record
ord-543de9c65f6e42f7ac21c2a1f2b683ee
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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