1,2-Dibromoethane → 1-(2-Bromoethoxy)-2-chloro-4-methylbenzene

HRID 734400Notes

Reaction equation

HRID 734400 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:10][CH2:11][CH2:12][O:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 148512-Chloro-4-methylphenol

Product 1

HCID 280653791-(2-Bromoethoxy)-2-chloro-4-methylbenzeneYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-chloro-4-methylphenol (500 mg, 3.62 mmol) in acetonitrile (20 mL) was added 1,2-dibromoethane (3.29 g, 17.53 mmol) followed by cesium carbonate (2.28 g, 7.01 mmol). The resulting mixture was heated at 85° C. for 48 h, then cooled to rt. The solution was filtered through a Celite® pad. The Celite® was washed with acetone and the combined eluents were concentrated under reduced pressure to give the title compound as a white solid (697 mg, 76%). GC/MS (EI) m/z 248 (M)+, RT 7.33 min.

Workup

  1. temperaturecooled to rt
  2. filtrationThe solution was filtered through a Celite® pad
  3. washThe Celite® was washed with acetone
  4. concentrationthe combined eluents were concentrated under reduced pressure

Sources & evidence

ORD record
ord-431602958460458cb0db8b1d6eafc049
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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