3-Methoxyacetophenone → Bromomethyl 3-methoxyphenyl ketone

HRID 885551Notes

Reaction equation

HRID 885551 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][CH2:10][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:11]

Participants

4

Reactant 2

HCID 114603-MethoxyacetophenoneHCID 24408Bromine

Product 1

HCID 101294Bromomethyl 3-methoxyphenyl ketoneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(3-methoxyphenyl)ethanone (5.5 mL, 40 mmol) in chloroform (100 mL) was added dropwise a solution of bromine (2.05 mL, 40 mmol) in chloroform (20 mL). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was diluted in methylene chloride (50 mL) and washed with water (2×25 mL). The organic layer was dried (Na2SO4) and the solvent removed under reduced pressure. Purification by column chromatography using methylene chloride as eluent gave the title compound (8.44 g, 84%) as oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted in methylene chloride (50 mL)
  3. washwashed with water (2×25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-3ebd80c86d9f4e9c856315f90927613c
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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