Potassium Iodide → 2-Fluoro-n-(2-nitrophenyl)aniline

HRID 1684518Notes

Reaction equation

HRID 1684518 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].[I-].[K+]>>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 95842-FluoroanilineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2613812-Fluoro-n-(2-nitrophenyl)aniline

Conditions

Temperature
23 °C

Procedure

A mixture of 2-fluoroaniline (13.0 ml), 2-fluoronitrobenzene (14.2 ml) and potassium iodide (5.5 g) was heated at 180° for 18 h. The mixture was cooled to 23° C.; the solid materials were filtered off and the solution was concentrated in vacuo. The residue was purified by flash chromatography (eluting with CH-EA 7:3) then crystallized from absolute ethanol to give the title compound as an orange solid (9.30 g). T.l.c. CH-EA (7:3), Rf =0.69. M.p. 76°-77° C. IR: 3352 (NH), 1609 (C=C), 1510 and 1350 (NO2) cm-1.

Workup

  1. temperaturewas heated at 180° for 18 h
  2. filtrationthe solid materials were filtered off
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (eluting with CH-EA 7:3)
  5. customthen crystallized from absolute ethanol

Sources & evidence

ORD record
ord-a79462df7db44a7abad5633d9cf433d3
Source dataset
uspto-grants-1997_06
Patent number
US05641775

Reaction notes

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