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

HRID 2103747Notes

Reaction equation

HRID 2103747 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(#N)C>[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

4

Reactant 2

HCID 171317-MethylcoumarinHCID 67184N-bromobutanimide

Product 1

HCID 2641197-(Bromomethyl)-2h-chromen-2-oneYield 101.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 7-methylcoumarin (50 g) in acetonitrile (1.2 L), N-bromosuccinimide (56 g) and α,α′-azobisisobutylonitrile (510 mg) were added, and the mixture was stirred for 30 minutes at 78° C. of inside temperature. The reaction mixture was concentrated, and water was added. The crystal was collected by filtration to give the title compound (76 g) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-3be1a31466a849f0953710979d31e01f
Source dataset
uspto-grants-2009_08
Patent number
US07576129B2

Reaction notes

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