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

HRID 1699015Notes

Reaction equation

HRID 1699015 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 a 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) δ7.30-7.09 (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-806985d3c4b948c09698230cb8d5a3ec
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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