3-Methoxyacetophenone → Bromomethyl 3-methoxyphenyl ketone

HRID 2424845Notes

Reaction equation

HRID 2424845 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-dbb770b6caa04079998fb59df39f4f89
Source dataset
uspto-grants-2011_06
Patent number
US07964615B2

Reaction notes

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