Acetonitrile → HCID 12850773, compound

HRID 1155748Notes

Reaction equation

HRID 1155748 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:13][C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[OH:24].C([O-])([O-])=O.[K+].[K+].C(#N)C>O>[F:13][C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[O:24][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 13041PentafluorophenolHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 12850773HCID 12850773, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen bubbler were placed 9.59 g (0.0525 moles) of 2-chloro-5-nitrobenzonitrile, 9.96 g (0.0541 moles) of 2,3,4,5,6-pentafluorophenol, 7.56 g (0.0541 moles) of anhydrous K2CO3, and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was then cooled to room temperature and diluted with 150 ml of deionized water. The product separated as a crystalline solid. The solid was filtered off, washed thoroughly with water, and air-dried. The air-dried solid was recrystallized from 200 ml of absolute ethanol to give 9.91 g (57% yield) of purified 2-(2,3,4,5,6-pentafluorophenoxy)-5-nitrobenzonitrile, mp 127.5°-129° C.

Workup

  1. customIn a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser
  2. customfitted with a nitrogen bubbler
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customThe product separated as a crystalline solid
  6. filtrationThe solid was filtered off
  7. washwashed thoroughly with water
  8. customair-dried
  9. customThe air-dried solid was recrystallized from 200 ml of absolute ethanol

Sources & evidence

ORD record
ord-26da3a5c9f254c5f88872db69412cb6d
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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