Benzoyl Peroxide → 1-(Bromomethyl)-2-fluoro-4-nitrobenzene

HRID 1428735Notes

Reaction equation

HRID 1428735 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:30][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 740252-Fluoro-4-nitrotoluene

Product 1

HCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzeneYield 88.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-fluoro-1-methyl-4-nitrobenzene (1 g, 6.446 mmol) in carbon tetrachloride was added benzoyl peroxide (497 mg, 1.2847 mmol) and N-bromosuccinimide (1.377 g, 7.736 mmol). The reaction mixture was refluxed for 18 h, then cooled to room temperature. The mixture was dissolved in ethyl acetate, then washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo to obtain 1-(bromomethyl)-2-fluoro-4-nitrobenzene (1.335 g) as a crude.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was removed in vacuo

Sources & evidence

ORD record
ord-5a7e8f8bf63c47b8bfedc97e70a07075
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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