Ethylene Glycol → 3-Fluoro-4-(2-hydroxyethoxy)benzonitrile

HRID 2078427Notes

Reaction equation

HRID 2078427 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1F)[C:11]#[N:12].[CH2:17]([OH:20])[CH2:18][OH:19]>>[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:19][CH2:18][CH2:17][OH:20])[C:11]#[N:12]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 5872033,4-DifluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 436574753-Fluoro-4-(2-hydroxyethoxy)benzonitrileYield 100%

Conditions

Temperature
50 °C

Procedure

To potassium tert-butoxide (19.35 g) was added ethylene glycol (160 mL). The mixture was then heated to 50° C. At 50° C., 3,4-difluorobenzonitrile (20 g) was added and this was washed in with ethylene glycol (40 mL). The combined solution was heated to 80° C., and held at this temperature for two hours, before being cooled to 20° C. over one hour. The reaction mixture was filtered and washed with ethylene glycol (40 mL). To the filtrate was added water (200 mL) and dichloromethane (200 mL). The layers were separated and the organic layer was concentrated in vacuo, to give the sub-title compound as a waxy white solid (26.1 g, 100% yield).

Workup

  1. washthis was washed in with ethylene glycol (40 mL)
  2. temperatureThe combined solution was heated to 80° C.
  3. temperaturebefore being cooled to 20° C. over one hour
  4. filtrationThe reaction mixture was filtered
  5. washwashed with ethylene glycol (40 mL)
  6. additionTo the filtrate was added water (200 mL) and dichloromethane (200 mL)
  7. customThe layers were separated
  8. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-f69f4b67b47c4aa4a1b4ecb53780308a
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

Loading…