Water → 4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzonitrile

HRID 918964Notes

Reaction equation

HRID 918964 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[CH2:11]([C:13]1[CH:14]=[C:15]([OH:22])[C:16]([O:20]C)=[CH:17][C:18]=1[F:19])[CH3:12].[OH-].[K+].O.[C:26](#N)C>>[CH2:11]([C:13]1[C:18]([F:19])=[CH:17][C:16]([O:20][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[F:1])=[C:15]([O:22][CH3:26])[CH:14]=1)[CH3:12]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 5872033,4-DifluorobenzonitrileHCID 67054849HCID 67054849, compound

Product 1

HCID 510347494-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzonitrile

Procedure

To 3,4-difluorobenzonitrile (12.26 g) dissolved in acetonitrile (10 volumes) was added 4-ethyl-5-fluoroguaiacol (15 g; which may be prepared as hereinbefore described for D2). Then, potassium hydroxide (0.33 parts) was added and the reaction mixture was refluxed for 7 hours. Once the reaction complete, the temperature was lowered to 20° C., water (2.5 volumes) was added and the phases separated. The organic phase was stored at RT until used in the next step.

Workup

  1. temperaturethe reaction mixture was refluxed for 7 hours
  2. customwas lowered to 20° C.
  3. customthe phases separated
  4. customwas stored at RT

Sources & evidence

ORD record
ord-8c64c8f349c5484c82fda75606eb9920
Source dataset
uspto-grants-2016_03
Patent number
US09272985B2

Reaction notes

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