1-(Bromomethyl)-2-chloro-4-iodobenzene → N-[(2-chloro-4-iodophenyl)methyl]phthalimide

HRID 885811Notes

Reaction equation

HRID 885811 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[Cl:10].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C)C=O.C(OCC)(=O)C>[Cl:10][C:4]1[CH:5]=[C:6]([I:9])[CH:7]=[CH:8][C:3]=1[CH2:2][N:15]1[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]2[C:11]1=[O:21]

Participants

5

Reactant 2

HCID 220586831-(Bromomethyl)-2-chloro-4-iodobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 66719866N-[(2-chloro-4-iodophenyl)methyl]phthalimideYield 72.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a solution of 7.6 g of 1-bromomethyl-2-chloro-4-iodobenzene in 50 mL of N,N-dimethylformamide, 3.7 g of potassium phthalimide was added, and stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was diluted with 80 mL of ethyl acetate, washed with water (30 mL×2), and then dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 5.7 g of the aimed product as white crystal.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with water (30 mL×2)
  3. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ff9861bdea4c4a8a9b68eeb9350659f4
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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