Benzoyl Peroxide → 7-(bromomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

HRID 2422483Notes

Reaction equation

HRID 2422483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[O:11][C:10](=[O:19])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:9][C:10](=[O:19])[O:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 569716744-(3-fluorophenyl)-7-methyl-2H-chromen-2-one

Product 1

HCID 597748617-(bromomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-(3-fluorophenyl)-7-methyl-2H-chromen-2-one (1.25 g, 4.9 mmol) in carbontetrachloride (30 mL), N-bromosuccinimide (963 mg, 5.41 mmol) and benzoylperoxide (60 mg, 0.25 mmol) were added. The reaction was then stirred overnight at reflux. After cooling, the reaction mixture was concentrated under reduced pressure. The crude residue obtained was purified on a short column of silica gel (eluting with CH2Cl2). The filtrate was concentrated and the solid obtained was swished in a mixture of CH2Cl2/hexanes. The title product was collected by filtration. 1H NMR (400 MHz, acetone-d6): 7.72-7.6 (m, 1H), 7.55 (s, 1H), 7.47 (s, 1H), 7.45-7.3 (m, 4H), 6.4 (s, 1H), 4.78 (s, 2H).

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ec1fc7ea3c547509c877eda9fe6c16d
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…