Potassium Carbonate → HCID 24697731, compound

HRID 523336Notes

Reaction equation

HRID 523336 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:2][CH2:3][CH2:4][C:5]#[N:6])=[CH:9][CH:10]=1)#[N:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 265484-Hydroxybenzyl cyanide

Product 1

HCID 24697731HCID 24697731, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

12.2 g (82.6 mmol) of 4-bromobutyronitrile, 10 g (95.1 mmol) of (4-hydroxyphenyl)acetonitrile and 31.1 g (225 mmol) of potassium carbonate are dissolved in 100 mL of DMF. The mixture is heated to 80° C. overnight. After 20 hours, the reaction mixture is partitioned between EtOAc and water. The organic phase is washed repeatedly with brine, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Purification by column chromatography on silica gel using ethylacetate:hexane 1:1 as eluent yields to 4.4 g of 4-[4-(cyanomethyl)phenoxy]butanenitrile as a thick yellow oil.

Workup

  1. customthe reaction mixture is partitioned between EtOAc and water
  2. washThe organic phase is washed repeatedly with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0d1fb1468ad4aa2bb3623c9f4fc99bf
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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