2-Bromo-1-(4-bromo-2-methoxyphenyl)ethanone → 4'-Bromo-2'-methoxy-2-(phthalimido)acetophenone

HRID 1993770Notes

Reaction equation

HRID 1993770 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[O:12][CH3:13])=[O:4].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C=O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:18]2[C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:24])=[C:6]([O:12][CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 223167792-Bromo-1-(4-bromo-2-methoxyphenyl)ethanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 591348634'-Bromo-2'-methoxy-2-(phthalimido)acetophenoneYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 6d (43.5 g) in anhydrous DMF (150 mL) was cooled to 5° C. To this solution was added potassium phthalimide (26.1 g, 141 mmol). After 5 min the cooling bath was removed and the reaction was allowed to stir at RT for 3 hr. The solvent was evaporated under vacuum to provide a tan solid. The solid was rinsed with 4:1 DCM/methanol and then water. The filter cake was slurried in toluene and evaporated to dryness to afford 4′-bromo-2′-methoxy-2-(phthalimido)acetophenone (compound 6e, 39 g) as a tan solid.

Workup

  1. customAfter 5 min the cooling bath was removed
  2. customThe solvent was evaporated under vacuum
  3. customto provide a tan solid
  4. washThe solid was rinsed with 4:1 DCM/methanol
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-1f0043050ad0428781eaed8d4909bcec
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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