Water → HCID 22148752, compound

HRID 1803843Notes

Reaction equation

HRID 1803843 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:21]=[C:22]([OH:27])[CH:23]=[C:24]([F:26])[CH:25]=1.O>CN(C=O)C>[F:19][C:20]1[CH:21]=[C:22]([CH:23]=[C:24]([F:26])[CH:25]=1)[O:27][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 759283,5-DifluorophenolHCID 37564675-Fluoro-2-nitrobenzonitrile

Product 1

HCID 22148752HCID 22148752, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-2-nitro-benzonitrile (5 g, 30.1 mmol) in dry DMF (60 mL) was treated first with cesium carbonate (11.7 g, 36.12 mmol) followed by 3,5-difluoro-phenol. The reaction was stirred at room temperature for 1 hour and then poured into iced water (600 mL). After stirring for 2 hours, a pale yellow solid was filtered with suction, washed with water furnishing, after drying at 50° C. under vacuum, 7.73 g of title compound in 93% yield.

Workup

  1. stirringAfter stirring for 2 hours
  2. filtrationa pale yellow solid was filtered with suction
  3. washwashed with water furnishing
  4. dry with materialafter drying at 50° C. under vacuum, 7.73 g of title compound in 93% yield

Sources & evidence

ORD record
ord-ab6847be23a04874ab13a4189c9c8f61
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

Loading…