Phthaloyl chloride → 2-Bromo-4,5-dimethoxyl-(2-phthalimidoethyl)benzene

HRID 388196

Reaction equation

HRID 388196 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][CH2:13][NH2:14].[C:15](Cl)(=[O:25])[C:16]1[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:18](Cl)=[O:19].CCN(C(C)C)C(C)C>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25]

Participants

5

Reactant 3

HCID 6955Phthaloyl chlorideHCID 81531DiisopropylethylamineHCID 8203702-Br-4,5-DMPEA

Product 1

HCID 50617422-Bromo-4,5-dimethoxyl-(2-phthalimidoethyl)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-4,5-dimethoxylbenzeneethanamine (3.5 g 13.2 mmol) was dissolved and stirred in 50 mL dry acetonitrile. 2.14 mL (1.1 equiv) phthaloyl dichloride and 7 mL (3 equiv) Hünig's base were added. The mixture was stirred at room temperature overnight. Acetonitrile was removed; the remaining product was taken up in dichloromethane and washed with basic water (pH=11). The aqueous wash was extracted with dichloromethane 15 mL×3. The organic fractions were combined and dried over sodium sulfate. Solvent was removed to give the crude product, which was then purified by column chromatography. Calculated yield: 1.8 g (34%).

Workup

  1. customAcetonitrile was removed
  2. washwashed with basic water (pH=11)
  3. washThe aqueous wash
  4. extractionwas extracted with dichloromethane 15 mL×3
  5. dry with materialdried over sodium sulfate
  6. customSolvent was removed

Sources & evidence

ORD record
ord-7ffb25b596854e6a8b23126d286b8475
Source dataset
uspto-grants-2013_02
Patent number
US08377704B2

Linked notes

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