Potassium Carbonate → (4-Bromo-2-ethylphenoxy)acetonitrile

HRID 858646

Reaction equation

HRID 858646 reaction equation
Br[CH2:2][C:3]#[N:4].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13][CH3:14])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:2][C:3]#[N:4])=[C:8]([CH2:13][CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 22688480(4-Bromo-2-ethylphenoxy)acetonitrileYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetonitrile (1.19 ml, 9.94 mmol) was added to a solution of 4-bromo-2-ethylphenol (2.0 g, 9.94 mmol) and potassium carbonate (1.35 g, 9.94 mmol) in DMF (50 ml). The reaction was stirred for 12 hours and then partitioned between diethyl ether (200 ml) and water (200 ml). The organics were separated, dried over magnesium sulfate, filtered and concentrated in vacuuo to afford the title compound as a yellow oil (2.0 g). 1H NMR (CDCl3): δ 1.13 (t, J=12.07 Hz, 3 H), 2.45 (m, 2H), 4.84 (s, 2H), 7.03–7.10 (m, 2H), 7.21 (m, 1H).

Workup

  1. custompartitioned between diethyl ether (200 ml) and water (200 ml)
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-6ab392d7872b45b79bcd1fcf7afc1b7d
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

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