Benzoyl Peroxide → 2-(Bromomethyl)-1-fluoro-3-nitrobenzene

HRID 1521655Notes

Reaction equation

HRID 1521655 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 698542-Fluoro-6-nitrotoluene

Product 1

HCID 747792-(Bromomethyl)-1-fluoro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 1-fluoro-2-methyl-3-nitrobenzene (1.0 g, 0.00645 mol) in carbon tetrachloride (50 mL) were added N-bromosuccinimide (1.25 g, 0.00709 mol) and benzoylperoxide (0.3 g, 0.00129 mol) at room temperature with constant stirring. Reaction mass was refluxed for 5 h. The reaction mixture was cooled to room temperature and filtered through CELITE bed and the bed was washed thoroughly with carbon tetrachloride. The filtrate was concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, DMSO) δ 7.93-7.91 (d, J=8 Hz, 1H), 7.723-7.653 (m, 2H), 4.77 (s, 2H).

Workup

  1. customReaction mass
  2. temperaturewas refluxed for 5 h
  3. filtrationfiltered through CELITE bed
  4. washthe bed was washed thoroughly with carbon tetrachloride
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-7d7c41e9e0014568854674dcd650ab7b
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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