Toluene → 7-bromo-4-(bromoacetyl)-2H-chromen-2-one

HRID 2116664Notes

Reaction equation

HRID 2116664 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([O:15]CC)=[CH2:14])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>C1COCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=[O:14])[CH2:15][Br:18])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 233702047-bromo-4-(1-ethoxyvinyl)-2H-chromen-2-one

Product 1

HCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-4-(1-ethoxyvinyl)-2H-chromen-2-one (2.0 g, 6.8 mmol) in THF and H2O was added N-bromosuccinimide (1.3 g, 14.2 mmol) and stirred for 30 min. Toluene was added and the solvent was evaporated. The residue was chromatographed on silica gel (hexane/EtOAc; 80:20) to give the title compound.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was chromatographed on silica gel (hexane/EtOAc; 80:20)

Sources & evidence

ORD record
ord-1d54f5f05d93454299555028a2c97d0f
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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