N-bromobutanimide → 1-(3-Bromoprop-1-en-2-yl)-4-fluorobenzene
Reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:18])=[CH2:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Br:1][CH2:17][C:16]([C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)=[CH2:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of N-bromo succinimide (8.6 g, 48.48 mmol) in chloroform (60 mL) was added 1-fluoro-4-isopropenyl-benzene (6 g, 44.11 mmol) at RT. The reaction mixture was stirred at 60° C. for 15 h. The progress of reaction was monitored by TLC. The reaction mixture was cooled to RT and filtered. The residue was rinsed with DCM (50 mL). The combined filtrate was concentrated under reduced pressure to obtain crude product that was purified by column chromatography using silica (100:200) and pure hexane to yield 4.2 g of 1-(1-bromomethyl-vinyl)-4-fluoro-benzene.
Workup
- customThe progress of reaction
- temperatureThe reaction mixture was cooled to RT
- filtrationfiltered
- washThe residue was rinsed with DCM (50 mL)
- concentrationThe combined filtrate was concentrated under reduced pressure
- customto obtain crude product that
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-c2e1f96130b044978b6891e7de798375
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040519B2
Reaction notes
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