Water → 3,5-Difluoro-4-[(4-iodo-1,3-dimethyl-1H-pyrazol-5-yl)oxy]benzonitrile

HRID 514232Notes

Reaction equation

HRID 514232 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[C:15]([F:16])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[F:17])=[CH:5][C:4]([CH3:18])=[N:3]1.[I:19]N1C(=O)CCC1=O.O>C(#N)C>[F:17][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([F:16])[C:8]=1[O:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([CH3:18])[C:5]=1[I:19])[C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 666124434-[(1,3-Dimethyl-1H-pyrazol-5-yl)oxy]-3,5-difluorobenzonitrile2×

Product 1

HCID 666121553,5-Difluoro-4-[(4-iodo-1,3-dimethyl-1H-pyrazol-5-yl)oxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[(1,3-dimethyl-1H-pyrazol-5-yl)oxy]-3,5-difluorobenzonitrile (i.e. the product of Step A) (1.38 g, 5.5 mmol) in acetonitrile (20 mL) was stirred at ambient temperature, and N-iodosuccinimide (1.35 g, 6.0 mmol) was added in one portion. The reaction mixture was heated at reflux for 2 h, cooled, and then poured into water (40 mL). The resulting mixture was extracted with ethyl acetate (40 mL). The organic phase was washed with water (20 mL) and saturated aqueous NaHCO3 solution (20 mL), dried over MgSO4, and concentrated under reduced pressure to give the title compound as a tan solid (2.1 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. extractionThe resulting mixture was extracted with ethyl acetate (40 mL)
  5. washThe organic phase was washed with water (20 mL) and saturated aqueous NaHCO3 solution (20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b66cdad1255c49cc9f77c58ed28fbf54
Source dataset
uspto-grants-2015_08
Patent number
US09107412B2

Reaction notes

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