Water → HCID 309016, compound

HRID 1756177Notes

Reaction equation

HRID 1756177 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:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Br)[CH:16]=1.C(OCC)C.O>CN(C)C=O>[Br:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH2:21][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 309016HCID 309016, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.57 g of potassium phthlimide was suspended in 20 ml of dimethylformamide, and 2.42 g of α,α'-dibromo-m-xylene was added. The mixture was stirred overnight at room temperature, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 0.52 g of N-(3-bromomethylbenzyl)phthalimide as a white crystalline powder.

Workup

  1. customThe organic layer separated
  2. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

Sources & evidence

ORD record
ord-d06c2194deba45b8b3e6d7e15029c0ec
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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