Dimethylformamide → 2-(2,6-Dichloro-4-methoxy-benzyl)-isoindole-1,3-dione

HRID 1670813Notes

Reaction equation

HRID 1670813 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=1[Cl:24].CN(C=O)C>C(OCC)(=O)C>[Cl:21][C:20]1[CH:19]=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([Cl:24])[C:15]=1[CH2:14][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 592994792-(Bromomethyl)-1,3-dichloro-5-methoxybenzene

Product 1

HCID 673536412-(2,6-Dichloro-4-methoxy-benzyl)-isoindole-1,3-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of potassium phthalimide (1.85 g, 10 mmol), 2-bromomethyl-1,3-dichloro-5-methoxy-benzene (2.68 g, 10 mmol) and DMF (20 mL) at 50° C. for 12 hours. Cool the reaction and dilute with ethyl acetate (60 mL) and wash with water three times and brine one time. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane to afford 2.74 g (82%) of the title compound. MS (m/z): 336 (M+H)+.

Workup

  1. temperatureCool
  2. customthe reaction
  3. washwash with water three times and brine one time
  4. dry with materialAfter drying the organic layer over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customPurify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane

Sources & evidence

ORD record
ord-584d755da8214bef87822affbb88cd81
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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