Tetrahydrofuran → N-(2-Fluorophenyl)formamide

HRID 1446773Notes

Reaction equation

HRID 1446773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[O:11]1CCC[CH2:12]1.[H][H].FC1C=CC=CC=1N>[Pd].C1(C)C=CC=CC=1.O.C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:12]=[O:11]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 95842-FluoroanilineHCID 738951-Fluoro-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 12803459N-(2-Fluorophenyl)formamide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 25 g of 2-fluoronitrobenzene, 250 ml of tetrahydrofuran and 0.5 of a commercial palladium catalyst (5% on charcoal) was hydrogenated (50 psig hydrogen pressure) in a Parr shaker at room temperature. A mixture of the 2-fluoroaniline thus formed and a ten percent molar excess of formic acid in toluene was refluxed for 2 hours, water of reaction being removed as formed. The resulting mixture was distilled to 90°-95° C., 0.05 Torr. On cooling, the product crystallized to give N-(2-fluorophenyl)formamide (1B), as a solid, m.p.: 47°-48° C.

Workup

  1. customat room temperature
  2. customthus formed
  3. custombeing removed
  4. customas formed
  5. distillationThe resulting mixture was distilled to 90°-95° C.
  6. temperatureOn cooling
  7. customthe product crystallized

Sources & evidence

ORD record
ord-08d08c5c11824feaa4827c83dc39f660
Source dataset
uspto-grants-1982_02
Patent number
US04313755

Reaction notes

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