N-bromobutanimide → 1-phenyl-8-fluoro-3-bromomethyl-2(1H)-quinolone

HRID 1108975Notes

Reaction equation

HRID 1108975 reaction equation
[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[F:17])[CH:10]=[C:9]([CH3:18])[C:8]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C1C=CC=CC=1>[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[F:17])[CH:10]=[C:9]([CH2:18][Br:20])[C:8]2=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 11229634Benzyl PeroxideHCID 190216391-phenyl-8-fluoro-3-methyl-2(1H)-quinolone

Product 1

HCID 190216381-phenyl-8-fluoro-3-bromomethyl-2(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reflux a solution of 1-phenyl-8-fluoro-3-methyl-2(1H)-quinolone (0.54 g), N-bromosuccinimide (0.38 g) and benzyl peroxide (0.04 g) in dry benzene (11 mL) for 6 hours. Evaporate, partition between dichloromethane and water, dry and evaporate the organic phase, and dry the residue at room temperature and high vacuum to obtain 1-phenyl-8-fluoro-3-bromomethyl-2(1H)-quinolone, suitable for further reactions (see example 32).

Workup

  1. customEvaporate
  2. custompartition between dichloromethane and water
  3. customdry
  4. customevaporate the organic phase
  5. customdry the residue at room temperature

Sources & evidence

ORD record
ord-d43f1b90e523426cabe6e9ad9ff3f23b
Source dataset
uspto-grants-1994_06
Patent number
US05318971

Reaction notes

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