Phthalimide → 2-(2-Bromo-4,6-dichlorobenzyl)isoindoline-1,3-dione

HRID 1481329Notes

Reaction equation

HRID 1481329 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10]Br.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CC#N>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][N:16]1[C:12](=[O:22])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:17]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 104260681-Bromo-2-(bromomethyl)-3,5-dichlorobenzene

Product 1

HCID 897047582-(2-Bromo-4,6-dichlorobenzyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-bromo-2-(bromomethyl)-3,5-dichlorobenzene (1.98 mmol) [J. Med. Chem., 35 (22), 4221 (1992)] in 10 mL CH3CN were added phthalimide (1.98 mmol) and K2CO3 (5.93 mmol). The reaction mixture was stirred at 50° C. for 6 h and then at RT overnight. Sat. aq. NaHCO3 solution was added and the mixture was extracted 3 times with DCM. The combined organic phases were dried over MgSO4 and concentrated in vacuo to obtain the desired product as beige solid.

Workup

  1. customat RT
  2. customovernight
  3. extractionthe mixture was extracted 3 times with DCM
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a933f82de4ac4c0abdc229076866e97c
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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