6-Methylcoumarin → 6-Bromomethyl-chromen-2-one

HRID 2253733Notes

Reaction equation

HRID 2253733 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2.C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 70926-MethylcoumarinHCID 67184N-bromobutanimide

Product 1

HCID 105141316-Bromomethyl-chromen-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 500 g (31.25 mmoles) of 6-methylcoumarin in 200 ml CCl4 is added 5.56 g (31.25 mmoles) of NBS. This solution is subjected to a sunlamp at reflux for 41/2 hours. After cooling, the reaction mixture is filtered and the filtrate concentrated in vacuo to yield a solid which upon trituration with ethyl acetate affords 6-bromomethylcoumarin which is used directly in the next step.

Workup

  1. temperatureat reflux for 41/2 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto yield a solid which upon trituration with ethyl acetate

Sources & evidence

ORD record
ord-b8fc8727fab245b39bf21d6e82863a8f
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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