7-Methylcoumarin → 7-(Bromomethyl)-2h-chromen-2-one

HRID 392604Notes

Reaction equation

HRID 392604 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 171317-MethylcoumarinHCID 67184N-bromobutanimide

Product 1

HCID 2641197-(Bromomethyl)-2h-chromen-2-oneYield 50.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent2×

Procedure

7-Methylcoumarin (28 g), 70% benzoylperoxide (1.68 g), and N-bromosuccinimide (30.8 g) was added to 140 mL chloroform in a one liter flask, and the suspension was refluxed overnight. The solution was diluted with 100 mL chloroform. The resulting crude product was recrystallized from 750 mL acetone. A white solid (21 g) with a melting point of 172-176° C. was obtained.

Workup

  1. temperaturethe suspension was refluxed overnight
  2. customThe resulting crude product was recrystallized from 750 mL acetone

Sources & evidence

ORD record
ord-2636686eddc04190b3aa5d093cae47f9
Source dataset
uspto-grants-2004_10
Patent number
US06800768B1

Reaction notes

Loading…