Potassium Carbonate → HCID 66667179, compound

HRID 1620320Notes

Reaction equation

HRID 1620320 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1F)[C:11]#[N:12].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=1>CS(C)=O.O>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:24][C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][C:20]=1[O:25][CH3:26])[C:11]#[N:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 280504-ChloroguaiacolHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 66667179HCID 66667179, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (0.784 g, 5.68 mmol) and 3-bromo-4-fluorobenzonitrile (0.378 g, 1.89 mmol) was added to a solution of 4-chloro-2-methoxyphenol (0.300 g, 1.89 mmol) in DMSO (7 mL). The reaction was heated at 80° C. for 2 hours, then cooled and left stirring at room temperature for 18 hours. The reaction was diluted with water (70 mL) and extracted with EtOAc (3×50 mL). The combined organics were washed with 1M NaOH aqueous solution (50 mL), brine (2×70 mL) and then dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as an off-white solid (0.625 g).

Workup

  1. temperaturecooled
  2. waitleft
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organics were washed with 1M NaOH aqueous solution (50 mL), brine (2×70 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6e33b022cb04632a26281f84e58485e
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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