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

HRID 890751Notes

Reaction equation

HRID 890751 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.C([Br:15])C=C.CCOC(C)=O>CC#N.[Cl-].[Na+].O>[Br:15][CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 99896673-(3-Chlorophenyl)propan-1-ol

Product 1

HCID 140848601-(3-Bromopropyl)-3-chlorobenzeneYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3-(3-chloro-phenyl)-propan-1-ol (12.54 g, 73.6 mmol) and N,N′-carbonyl diimidazole (13.12 g, 81 mmol) in CH3CN was stirred at room temperature for 1 h. Allyl bromide (53.43 g, 442 mmol) was added and the reaction was heated at reflux for 24 h. The reaction was cooled to room temperature and brine and EtOAc were added. The aqueous solution was extracted with EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography provided the title compound in about 85% yield. 1H NMR (400 MHz, CDCl3) δ 7.30–7.09 (m, 4H), 3.38 (t, 2H), 2.76 (t, 2H), 2.15 (t, 2H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 h
  3. extractionThe aqueous solution was extracted with EtOAc
  4. dry with materialthe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e1efa842e824e08982272ff72b654e9
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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