N-bromobutanimide → 3-bromomethyl-9H-xanthen-9-one

HRID 355425Notes

Reaction equation

HRID 355425 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 4703953-Methylxanthen-9-one

Product 1

HCID 107797593-bromomethyl-9H-xanthen-9-oneYield 98.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methyl-9H-xanthen-9-one (1.62 g, 7.71 mmol), N-bromosuccinic acid imide (1.37 g, 7.71 mmol), benzoyl peroxide (93 mg, 0.39 mmol) and carbon tetrachloride (15 ml) was heated under reflux for 15 hours. The insoluble matter was removed by filtration and the resulting filtrate was concentrated under a reduced pressure to give 3-bromomethyl-9H-xanthen-9-one (2.19 g, 7.57 mmol, 98%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe resulting filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-9eb3816249df4e0fafc992fc3795d6c2
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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