2,4-Difluoronitrobenzene → 5-fluoro-N-(1-(3,5-dimethylphenyl)ethyl)-2-nitrobenzenamine

HRID 2426013Notes

Reaction equation

HRID 2426013 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]([NH2:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.F[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].C(N(CC)C(C)C)(C)C>C(#N)C>[F:19][C:17]1[CH:16]=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[C:13]([NH:11][CH:9]([C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH3:10])[CH:18]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 231477461-(3,5-Dimethylphenyl)ethanamine

Product 1

HCID 587073365-fluoro-N-(1-(3,5-dimethylphenyl)ethyl)-2-nitrobenzenamineYield 67.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3,5-Dimethylphenyl)ethanamine (670 mg, 4.2 mmol), 2,4-difluoronitrobenzene (764 mg, 4.2 mmol) and N,N-diisopropylethylamine (1.08 mg, 8.4 mmol) were stirred at room temperature in dry acetonitrile (50 mL) for 6 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated to collect the title compound (820 mg, 61% yield). 1H NMR (400 MHz, CDCl3): δ 8.49 (s, 1H), 8.19 (m, 1H), 6.45 (s, 2H), 6.30 (m, 3H), 4.48 (m, 1H), 3.76 (s, 6H), 1.62 (d, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated

Sources & evidence

ORD record
ord-ff6575bba7c6488ab68497271c674762
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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