3',4',5'-Trimethoxyacetophenone → 2-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

HRID 618080Notes

Reaction equation

HRID 618080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1CNC(=O)C1.[Br:22][Br-]Br>O1CCCC1>[Br:22][CH2:14][C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15]

Participants

3

Reactant 1

HCID 143453',4',5'-Trimethoxyacetophenone

Product 1

HCID 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanoneYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

3',4',5'-Trimethoxyacetophenone (15.0 g) and pyrrolidone hydrotribromide (35.39 g) were dissolved in tetrahydrofuran (225 ml), followed by stirring at 40° C. for one hour. The reaction solution was cooled to room temperature, precipitated crystals were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained crude crystals were washed with hexane (100 ml) to give 2-bromo-3',4',5'-trimethoxyacetophenone (Compound XIa, 12.20 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customprecipitated crystals
  3. filtrationwere filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customthe obtained crude crystals
  7. washwere washed with hexane (100 ml)

Sources & evidence

ORD record
ord-0b230950158c4ee38d667994500d094c
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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