Ethanol → 4-Bromo-2-ethoxybenzonitrile

HRID 1897768Notes

Reaction equation

HRID 1897768 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([OH:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:19][CH2:17][CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 595783964-Bromo-2-ethoxybenzonitrileYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-Bromo-2-fluoro-benzonitrile (5 g, 25.00 mmol), potassium carbonate (10.37 g, 75.0 mmol), ethanol (6.86 mL, 117 mmol) in DMF (50 mL) was heated at 60° C. for overynight. After filtration and concentration, the residue was dissolved in ethyl acetate (150 mL), and the solution was washed with water (30 mL) and brine (50 mL). After drying over Na2SO4, filtration and concentration, a light brown solid (5.7 g) was obtained without further purification. 1H NMR (400 MHz, CDCl3): δ 1.49 (t, J=7 Hz, 3H), 4.14 (q, J=7 Hz, 2H), 7.11 (d, J=1.7 Hz, 1H), 7.14 (dd, J=8.1, 1.7 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H).

Workup

  1. filtrationAfter filtration and concentration
  2. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  3. washthe solution was washed with water (30 mL) and brine (50 mL)
  4. dry with materialAfter drying over Na2SO4, filtration and concentration

Sources & evidence

ORD record
ord-71ebdd7a86da4785a99dab6ebb5957b1
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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