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

HRID 1726327Notes

Reaction equation

HRID 1726327 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>>[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

3

Reactant 2

HCID 171317-MethylcoumarinHCID 67184N-bromobutanimide

Product 1

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

Conditions

Temperature
78 °C

Procedure

To a solution of 7-methylcoumarin (50 g) in acetonitorile (1.2 L) were added N-bromosuccinimide (56 g) α,α′-azobisisobutyronitrile (510 mg) and the mixture was stirred at 78° C. for 30 minutes. The reaction solution was concentrated and then added water (1 L). The appeared crystal was filtrated to give the title compound (76 g) having the following physical data.

Workup

  1. concentrationThe reaction solution was concentrated
  2. filtrationThe appeared crystal was filtrated

Sources & evidence

ORD record
ord-b636dde1d76f47f8884088a91a07c032
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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