Phenol → HCID 66667120, compound

HRID 1620336Notes

Reaction equation

HRID 1620336 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]#[N:6]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 66667120HCID 66667120, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-4-fluorobenzonitrile (0.5 g, 2.4 mmol) was added to a suspension of phenol (0.23 g, 2.4 mmol) and potassium carbonate (0.67 g, 4.8 mmol) in DMSO (2 mL) and the reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was diluted with EtOAc (30 mL) and washed with water (3×30 mL). The combined organics were dried over sodium sulfate and concentrated in vacuo to afford the title compound (0.59 g).

Workup

  1. washwashed with water (3×30 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cf42323180543b48e48378595a79b14
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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