2-Isopropylaniline → HCID 59359507, compound

HRID 383206Notes

Reaction equation

HRID 383206 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].[F-].[K+]>O>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 125612-IsopropylanilineHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 59359507HCID 59359507, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

2-isopropylaniline (27 g, 200 mmol), 2-fluoronitrobenzene (14 g, 100 mmol), and potassium fluoride (8.6 g, 150 mmol) were mixed in a one-neck flask. The mixture was heated up to 180° C. under nitrogen for 48 hours. After cooled to room temperature, water (200 mL) was added. The mixture was then extracted with dichloromethane (200 mL) for three times. The solvent was evaporated and the residue was purified by column chromatography using 20% of dichloromethane in hexanes. 22.5 g of desired product was obtained.

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionThe mixture was then extracted with dichloromethane (200 mL) for three times
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-517e366629414442996c473beb89684d
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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