Allyl bromide → 1-(3-Bromopropyl)-3-methoxybenzene

HRID 413423Notes

Reaction equation

HRID 413423 reaction equation
[CH2:1]([Br:4])[CH:2]=[CH2:3].[CH3:5][O:6][C:7]1[CH:8]=[C:9](CCCO)[CH:10]=[CH:11][CH:12]=1>CC#N>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:3][CH2:2][CH2:1][Br:4])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 961303-m-Anisyl-1-propanol

Product 1

HCID 1388771-(3-Bromopropyl)-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Allyl bromide (25 mL, 0.28 mmol) was added to a solution of 3-(3-methoxyphenyl)propanol (8.8 g, 0.053 mol), N,N′-carbonyldiimidazole (9.6 g, 0.0605 mol) and CH3CN (45 mL) at room temperature. After 1.5 hr at rt and 1.5 hr at reflux, the reaction mixture was cooled, partitioned between EtOAc (250 mL) and H2O (300 mL), the organic layer washed with H2O (300mL), 5% HCl (200 mL), dilute NaHCO3 solution (200 mL), brine (300 mL), and dried (Na2SO4). Filtration and concentration to dryness gave the title compound.

Workup

  1. temperature1.5 hr at reflux
  2. temperaturethe reaction mixture was cooled
  3. custompartitioned between EtOAc (250 mL) and H2O (300 mL)
  4. washthe organic layer washed with H2O (300mL), 5% HCl (200 mL), dilute NaHCO3 solution (200 mL), brine (300 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-4da935f8521041f7a3b37025811368e2
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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