N-bromobutanimide → HCID 19006240, compound

HRID 1743039Notes

Reaction equation

HRID 1743039 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[C:3]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24].[Br:26]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:26][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[C:3]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19006254HCID 19006254, compound

Product 1

HCID 19006240HCID 19006240, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-methyl-2,3-bis(acetoxymethyl)-6,7-dimethoxynaphthalene (5.0 g) in carbon tetrachloride (100 ml) are added N-bromosuccinimide (2.8 g) and benzoyl peroxide (150 mg), and the mixture is refluxed for 2 hours. The mixture is allowed to cool, and the insoluble materials are separated by filtration, and the filtrate is concentrated under reduced pressure to give 1-bromomethyl-2,3-bis(acetoxymethyl)-6,7-dimethoxynaphthalene (5.1 g) as crystal.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperatureto cool
  3. customthe insoluble materials are separated by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5e95d3813a404043a567cd12e74db12a
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Reaction notes

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