3'-Bromoacetophenone → HCID 57825051, compound

HRID 1668704Notes

Reaction equation

HRID 1668704 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]2[O:9][CH2:10][O:11][C:5]=2[CH:4]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)=O>O1CCCC1.BrBr>[Br:21][C:17]1[CH:16]=[C:15]([C:13]([C:3]2[CH:8]=[CH:7][C:6]3[O:9][CH2:10][O:11][C:5]=3[CH:4]=2)=[CH2:12])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 165023'-BromoacetophenoneHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5462224Magnesium

Product 1

HCID 57825051HCID 57825051, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 24408BromineSolvent

Procedure

To a mixture of magnesium turnings (440 mg, 0.01 mol, 1.2 eq) in dry tetrahydrofuran (5 mL), was added 4-bromo-1,2(methylendioxy)benzene (3.1 g, 0.01 mol, 1.1 eq) in dry tetrahydrofuran (10 mL) and bromine (0.5 mL). The resulting solution was refluxed for 2 hours. Then the mixture was cooled at room temperature and a solution of 3-bromoacetophenone (3.0 g, 0.01 mol, 1 eq) in dry tetrahydrofuran (10 mL) was added dropwise and refluxed. After 3 hours the reaction mixture was examined by LC-MS which showed complete conversion to the desired product. The mixture was quenched with 1 M HCl solution (20 mL). The aqueous phase was extracted with ethyl acetate. (3×20 mL), dried (sodium sulfate) and the solvent removed in vacuo. The crude was dissolved in toluene (30 mL) and a catalytic amount of p-toluenesulfonic acid was added. The mixture was heated to reflux for 3 h (using a Dean-Stark water trap). The solvent was removed and the residue was purified by column chromatography (cyclohexane) to afford the title compound as a colorless oil (3.7 g, 80%);

Workup

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. temperaturerefluxed

Sources & evidence

ORD record
ord-18068aa56df344c28ffdc56a732eb0d3
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

Loading…