1,2-Dibromoethane → 4-(2-Bromoethoxy)benzonitrile

HRID 1928544Notes

Reaction equation

HRID 1928544 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Br:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[Br:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 24522124-(2-Bromoethoxy)benzonitrileYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture of 4-hydroxybenzonitrile (1.19 g, 10 mmol), 1,2-dibromoethane (9.39 g, 50 mmol), and K2CO3 (4.14 g, 30 mmol) in DMF (20 mL) was stirred at 100° C. for 5 h and cooled to room temperature. To the reaction mixture was added ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography to afford the 4-(2-bromoethoxy)benzonitrile (1.2 g, 53%).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-400d387c1cca435aa82ee6848b70850f
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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