Allyl bromide → 1-Allyl-4-fluorobenzene

HRID 1799528Notes

Reaction equation

HRID 1799528 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

HCID 7841Allyl bromideHCID 178418676HCID 178418676, compound

Product 1

HCID 111477491-Allyl-4-fluorobenzene

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

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

  1. customThe layers were separated
  2. washthe organic layer was washed with water (25 mL) and brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66100db13b5442d9a0ec20c7036bd7d3
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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