Allyl bromide → 1-Allyl-4-fluorobenzene
Reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1>O1CCCC1.C(OCC)C.[Cl-].[NH4+]>[CH2:3]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)[CH:2]=[CH2:1]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
Allyl bromide (4.33 mL, 50 mmol) was added dropwise to a solution of 4-fluorophenyl magnesium bromide (50 mmol) in tetrahydrofuran (25 mL) and diethyl ether (25 mL). After 16 hours, the reaction suspension was diluted with diethyl ether (100 mL) and saturated aqueous ammonium chloride (50 mL). The layers were separated, and the organic layer was washed with water (25 mL) and brine (25 mL), dried over magnesium sulfate, filtered, and concentrated to afford 1-allyl-4-fluorobenzene.
Workup
- customThe layers were separated
- washthe organic layer was washed with water (25 mL) and brine (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-66100db13b5442d9a0ec20c7036bd7d3
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344144B2
Reaction notes
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