1,2-Bis(chloromethyl)benzene → N-(2-chloromethylbenzyl)phthalimide

HRID 1032912Notes

Reaction equation

HRID 1032912 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[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]>>[C:11]1(=[O:21])[N:15]([CH2:2][C:3]2[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12

Participants

3

Reactant 2

HCID 119191,2-Bis(chloromethyl)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 57925620N-(2-chloromethylbenzyl)phthalimide

Conditions

Temperature
50 °C

Procedure

A mixture of α,α'-dichloroxylene (8.75 g, 50 mmol) and potassium phthalimide (5.6 g, 30 mmol) was heated to 50° C. for 24 h. Then the reaction mixture was concentrated in vacuo, dissolved in ethyl acetate and, after usual work-up, the desired compound was obtained by flash chromatography on silica gel (ethyl acetate:hexane; 15:85) (6 g, 65%).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate

Sources & evidence

ORD record
ord-b59343413fe04eaab5fe9f1a8b5db9ba
Source dataset
uspto-grants-1994_05
Patent number
US05308837

Reaction notes

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