Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-2-fluorobenzene
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[Br:8].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Br:8])[CH2:9][Br:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
3-Fluoro-4-bromotoluene (5.0 g, 27 mmol) in carbon tetrachloride (50 mL) was treated with N-bromosuccinimide (7.0 g, 40 mmol, 1.5 eq) and heated to 80° C. Benzoyl peroxide (65 mg, 0.27 mmol, 0.01 eq.) was added and heating was continued for 1 h. The reaction was then cooled to ambient temperature and filtered, and the filtercake was washed sparingly with chloroform. The filtrate was washed with water and brine, dried over Na2SO4, and concentrated to give crude 3-fluoro-4-bromobenzyl bromide as a clear oil which was used without further purification.
Workup
- temperatureheating
- temperatureThe reaction was then cooled to ambient temperature
- filtrationfiltered
- washthe filtercake was washed sparingly with chloroform
- washThe filtrate was washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-43932dd6b1aa4865bfbd8dbc1c5047b6
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957049B2
Reaction notes
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