Benzoyl Peroxide → Methyl 7-(bromomethyl)-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylate

HRID 922798Notes

Reaction equation

HRID 922798 reaction equation
[F:1][C:2]1[C:3]([CH3:23])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:49])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:49][CH2:23][C:3]1[C:2]([F:1])=[C:11]2[C:6]([C:7]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 89543914Methyl 8-fluoro-4-(4-fluorophenyl)-7-methylquinoline-2-carboxylate

Product 1

HCID 89554976Methyl 7-(bromomethyl)-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 8-fluoro-4-(4-fluorophenyl)-7-methylquinoline-2-carboxylate 7-9 (991 mg, 3.16 mmol), Benzoyl peroxide (102 mg, 0.316 mmol), and NBS (591 mg, 3.32 mmol) were heated at reflux in CCl4 for 5 hours. The solvent was removed in vacuo and the residue purified by column chromatography on a silica gel column, eluting with EtOAc/hexane (0-50%) to afford Methyl 7-(bromomethyl)-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylate 7-10 (1.05 g, 85% yield) as a white solid, LCMS shows the compound is 67% pure, LRMS m/z (M+H)+ 392.0 found, 392.1 required.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by column chromatography on a silica gel column
  3. washeluting with EtOAc/hexane (0-50%)

Sources & evidence

ORD record
ord-cbfcaacf7fbe48bcb040ed96da18a80e
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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