Potassium Carbonate → 3-(3-Bromo-5-chlorophenoxy)-4-chloropyridine-2-carbonitrile

HRID 1952380Notes

Reaction equation

HRID 1952380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[C:3]=1F.[Br:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:19][C:3]1[C:4]([C:8]#[N:9])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226301803-Bromo-5-chlorophenolHCID 595297654-Chloro-3-fluoro-2-pyridinecarbonitrile

Product 1

HCID 595297833-(3-Bromo-5-chlorophenoxy)-4-chloropyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-chloro-3-fluoropyridine-2-carbonitrile (2.18 g, 9.03 mmol) in DMF (10 mL) was added 3-bromo-5-chlorophenol (1.96 g, 9.48 mmol) and potassium carbonate (1.25 g, 9.03 mmol) and the mixture was heated to 55° C. for 10 minutes. The mixture was cooled to room temperature and partitioned between water (200 mL) and ethyl acetate (2×100 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvent evaporated in vacuo to provide the title compound. LRMS (M+1): 344.8

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water (200 mL) and ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cd9ff8035e7b4605ae9166d93bfcef24
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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