Potassium Carbonate → HCID 19086726, compound

HRID 1464570Notes

Reaction equation

HRID 1464570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([F:9])[C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]>CN(C=O)C.CC(CC(C)=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([F:9])[C:7]=1[O:27][C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[C:22]([N+:28]([O-:30])=[O:29])[CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresolHCID 2736496Benzene, 1-chloro-2,3-difluoro-5-(trifluoromethyl)-

Product 1

HCID 19086726HCID 19086726, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

3-Chloro-4,5-difluorobenzotrifluoride (99 g) was dissolved in dry MBIK (100 cm3) and 25 drops of dry DMF and dry potassium carbonate (48 g) added. The mixture was stirred and brought to reflux when a solution of 4-methyl-3-nitrophenol (35 g) in dry MIBK (70 cm3) was added over 1 hour. When the addition was complete stirring and reflux were continued for 2 hours. The solvent was removed from the reaction mixture under vacuum and the residue triturated with water (500 cm3). The solid obtained was filtered off, washed with water and air dried. The crude solid was recrystallised from ethanol to give 4-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2-nitrotoluene (73.5 g) as an off white solid, m.p. 112.8°-115.4° C.

Workup

  1. additionadded
  2. additionwas added over 1 hour
  3. additionWhen the addition
  4. stirringwas complete stirring
  5. temperaturereflux
  6. customThe solvent was removed from the reaction mixture under vacuum
  7. customthe residue triturated with water (500 cm3)
  8. customThe solid obtained
  9. filtrationwas filtered off
  10. washwashed with water and air
  11. customdried
  12. customThe crude solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-bdd109b0bc1845d3b23ec67c7a8d1140
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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