Ethyl Bromide → 2-Ethoxy-4-nitro-benzonitrile

HRID 1754512Notes

Reaction equation

HRID 1754512 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:21]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 2861482-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 214837232-Ethoxy-4-nitro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-4-nitrobenzonitrile (0.5 g, 3.04 mmol) in DMF (5 ml) is added-potassium carbonate (0.631 g, 4.56 mmol) followed by bromoethane (0.238 ml, 3.19 mmol) and the reaction mixture is stirred at room temperature for 5 days. The solvent is removed in vacuo and the crude is partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer is separated, washed with water (2×100 ml), saturated sodium hydrogen carbonate solution (100 ml) and concentrated in vacuo to afford the titled compound as a pale yellow solid which is used crude in the next step.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude is partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. customThe organic layer is separated
  4. washwashed with water (2×100 ml), saturated sodium hydrogen carbonate solution (100 ml)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f83e34358eb42b3b22713721ab5ea50
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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