Sodium Bicarbonate → 2-Bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one

HRID 56586Notes

Reaction equation

HRID 56586 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:4][C:3]=1[O:14][CH3:15].[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:16][CH:11]([CH3:12])[C:10]([C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Br:1])=[C:3]([O:14][CH3:15])[CH:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21124087PyridiniumtribromideHCID 584320651-(4-Bromo-3,5-dimethoxyphenyl)propan-1-one

Product 1

HCID 584320252-Bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-oneYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one (1.50 g, 5.49 mmol) in anhydrous THF (20 mL) was added pyridinium tribromide (1.93 g, 6.04 mmole). The reaction was stirred at room temperature for 2 hrs then neutralized with a solution of saturated aqueous NaHCO3. The mixture was extracted with EtOAc the combined organics were washed with saturated aqueous NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (10-20% EtOAc-hexanes) gave 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one as an orange oil (1.09 g, 56% yield).

Workup

  1. extractionThe mixture was extracted with EtOAc the combined
  2. washorganics were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialthen dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (10-20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-1523efd715ef4d52956632cd0dafdea7
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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