Water → 5-[(3,5-Difluorobenzyl)oxy]-2-nitrobenzonitrile

HRID 1803839Notes

Reaction equation

HRID 1803839 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].[F:13][C:14]1[CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=[C:18]([F:20])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:13][C:14]1[CH:15]=[C:16]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH2:21][O:22][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 5227213,5-Difluorobenzyl alcoholHCID 37564675-Fluoro-2-nitrobenzonitrile

Product 1

HCID 669962345-[(3,5-Difluorobenzyl)oxy]-2-nitrobenzonitrileYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzonitrile (60 g, 354 mmol), (3,5-difluorophenyl)methanol (52.14 mL, 460 mmol) and cesium carbonate (155 g, 460 mmol) in dry DMF (720 mL) was stirred at 70° C. for 6 hours. The reaction mixture was cooled at room temperature and poured into water (7 L) under stirring. The so obtained precipitated was filtered, washed with water and dried under vacuum at 50° C., affording 95 g (yield 92%) of the title compound.

Workup

  1. customThe so obtained
  2. customprecipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-79c0ae55fd1240229950c82d9822a352
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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