4-Chlorophenol → HCID 66667775, compound

HRID 1620329Notes

Reaction equation

HRID 1620329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:18][C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=1)[C:5]#[N:6]

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 66667775HCID 66667775, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 3-bromo-4-fluorobenzonitrile (1.60 g, 8.00 mmol), 4-chlorophenol (1.028 g, 8 mmol) and potassium carbonate (2.487 g, 24 mmol) in DMSO (20 mL) was stirred for 18 hours at room temperature under a nitrogen atmosphere. The reaction was diluted with aqueous ammonium chloride (50 mL) and extracted with EtOAc (3×30 mL). The combined organic extract was washed with water (2×30 mL) and dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a white solid (2.47 g).

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water (2×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe09c13f80dd48f6a37719e3ee6e69bf
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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