p-Fluoronitrobenzene → HCID 20187571, compound

HRID 2308739Notes

Reaction equation

HRID 2308739 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:17])[CH:10]([F:16])[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[OH-].[Na+].[N+:20]([C:23]1[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=1)([O-:22])=[O:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:17][C:26]1[CH:27]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=1)[CH:10]([F:16])[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 20187544HCID 20187544, compound

Product 1

HCID 20187571HCID 20187571, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

With efficient stirring, 27.6 g of 1-(2,4-dichlorophenyl)-2-fluoro-2-(1H-1,2,4-triazolyl)ethanol (prepared in accordance with Example P1a) were added to a mixture of 250 ml of 2n NaOH solution, 250 ml of diethyl ether and 0.5 g of tetrabutylammonium bromide. 25 ml of 4-nitrofluorobenzene are added at 20° C. to this mixture, which is stirred for another 20 hours at room temperature. The separated ethereal phase is washed with water until neutral, dried over sodium sulfate, filtered and concentrated by evaporation. The crude oily product (35 g) is purified by chromatography through silica gel and melts after recrystallisation from diisopropyl ether/cyclohexanone at 98°-100° C.

Workup

  1. washThe separated ethereal phase is washed with water until neutral,
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe crude oily product (35 g) is purified by chromatography through silica gel and melts
  6. customafter recrystallisation from diisopropyl ether/cyclohexanone at 98°-100° C.

Sources & evidence

ORD record
ord-72eb79977e9441e5ab2bfda5f824de94
Source dataset
uspto-grants-1987_09
Patent number
US04690942

Reaction notes

Loading…