Methanol → Methyl 4-(2-bromoacetyl)benzoate

HRID 1060999Notes

Reaction equation

HRID 1060999 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:14]Br.CO.O>C(O)(=O)C.Br>[Br:14][CH2:2][C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24408BromineHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 13612771Methyl 4-(2-bromoacetyl)benzoateYield 71%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
15 °C

Procedure

At 15° C., methyl 4-acetylbenzoate (2.23 g) was dissolved in a hydrobromic acid acetic acid solution (30%, 10 ml). Bromine was gradually added dropwise to the reaction mixture to maintain its temperature at 15° C. After stirring for 10 minutes, the reaction mixture was cooled to 4° C. A mixed solvent of methanol (50 ml) and water (50 ml) was added to the reaction mixture for crystallization, followed by washing with hexane. By the collection through filtration, the title compound (2.29 g, 71%) was obtained as a colorless solid.

Workup

  1. temperaturethe reaction mixture was cooled to 4° C
  2. washby washing with hexane
  3. customBy the collection
  4. filtrationthrough filtration

Sources & evidence

ORD record
ord-a7cff0208412433e9a8f52a062c4df10
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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