Potassium Carbonate → HCID 59548943, compound

HRID 1184366Notes

Reaction equation

HRID 1184366 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[OH:27]>C1COCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[O:27][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 949522,5-Difluorophenol

Product 1

HCID 59548943HCID 59548943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-3-nitrobenzonitrile (5 g) in THF (200 mL) at room temperature was treated with K2CO3 (19 g), followed by 2,5-difluorophenol (3.7 g). After stirring at room temperature for 18 hrs, the solid was filtered off and rinsed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated aqueous NaHCO3 solution, water, and saturated aqueous NaCl solution, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residual was triturated with hexanes and collected by suction to furnish the desired product 21, which was used directly in the next step without further purification.

Workup

  1. filtrationthe solid was filtered off
  2. washrinsed with copious amounts of EtOAc
  3. washThe filtrate was washed sequentially with saturated aqueous NaHCO3 solution, water, and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual was triturated with hexanes
  8. customcollected by suction

Sources & evidence

ORD record
ord-f09f890cb9c1413dbe399ff8ad1eb362
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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