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

HRID 899120Notes

Reaction equation

HRID 899120 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[Br:16][CH2:17][CH2:18]Br>CN(C=O)C.O>[Br:16][CH2:17][CH2:18][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 24522124-(2-Bromoethoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

Anhydrous potassium carbonate (233 g, 1.68 mol) was added to a solution of 4-hydroxybezonitrile (100 g, 0.84 mol) in DMF (700 mL), and the resultant mixture was stirred for 1 h under a N2 atmosphere. 1,2-Dibromo-ethane (362 mL, 4.2 mol) was added slowly to the reaction mixture, which was then stirred at 55-60° C. overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3×750 mL). The combined organic layer was washed with water and then concentrated. The crude product was purified by column chromatography (silica gel: 60-120 mesh, eluent: petroleum ether-ethyl acetate, 90:10). Yield: 60 g (32%).

Workup

  1. extractionextracted with ethyl acetate (3×750 mL)
  2. washThe combined organic layer was washed with water
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel: 60-120 mesh, eluent: petroleum ether-ethyl acetate, 90:10)

Sources & evidence

ORD record
ord-64cb12b1aace4f1ea0569c2e7c9a1488
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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