2-Fluoroaniline → 2-Fluoro-n-(2-nitrophenyl)aniline

HRID 1818769Notes

Reaction equation

HRID 1818769 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2613812-Fluoro-n-(2-nitrophenyl)anilineYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoroaniline (1.45 mL, 15 mmol) was dissolved in DMF (10 mL) and sodium hydride (0.58 g, 15 mmol) was added and the mixture was stirred for 30 minutes. 2-Fluoronitrobenzene (1.05 mL, 10 mmol) was added and the mixture was stirred for 16 hours. The mixture was quenched with saturated NH4Cl and diluted with ether. The mixture was washed with water, brine, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified via Isco chromatography (Redisep, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.4 g 2-fluoro-N-(2-nitrophenyl)aniline that was carried on directly to the next step. MS (ES) m/z 232.9.

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. customThe mixture was quenched with saturated NH4Cl
  3. additiondiluted with ether
  4. washThe mixture was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 5-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e2586e9d43c84e8888da876a19761053
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

Loading…