Oxyselenide → 6-Bromo-7-acetoxy-4-formylcoumarin

HRID 993359Notes

Reaction equation

HRID 993359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13](=[O:15])[CH3:14])[O:8][C:7](=[O:16])[CH:6]=[C:5]2[CH3:17].[Se]=[O:19]>C1(C)C=CC=C(C)C=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13](=[O:15])[CH3:14])[O:8][C:7](=[O:16])[CH:6]=[C:5]2[CH:17]=[O:19]

Participants

4

Reactant 2

HCID 167175OxyselenideHCID 184103326-Bromo-7-acetoxy-4-methylcoumarin

Product 1

HCID 184103366-Bromo-7-acetoxy-4-formylcoumarinYield 67.7%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A mixture of 404.9 mg (1.363 mmol) of compound 18, 239.2 mg (2.156 mmol) of selenium oxide in m-xylene (15 mL) was stirred under refluxed temperature for 21 hours. The reaction mixture was cooled and evaporated. Purification by column chromatography gave 287.0 mg (0.9226 mmol, 67.7% yield) of compound 19.

Workup

  1. temperatureunder refluxed temperature for 21 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-79692a787dda457dab549e08bae68c6a
Source dataset
uspto-grants-2002_10
Patent number
US06472541B2

Reaction notes

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