2,4-Difluoronitrobenzene → 5-Fluoro-n-(2-methyl-1-phenylpropyl)-2-nitrobenzenamine

HRID 2425997Notes

Reaction equation

HRID 2425997 reaction equation
[CH3:1][CH:2]([CH3:11])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:4].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:4][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([CH3:11])[CH3:1])[CH:18]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 49628752-Methyl-1-phenylpropan-1-amine

Product 1

HCID 587072515-Fluoro-n-(2-methyl-1-phenylpropyl)-2-nitrobenzenamineYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-methyl-1-phenylpropan-1-amine (1.0 g, 6.7 mmol), 2,4-difluoronitrobenzene (0.74 mL, 6.7 mmol) and N,N-diisopropylethylamine (2.3 mL, 13.4 mmol) in acetonitrile was stirred at room temperature for 32 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water, dried, and concentrated under reduced pressure to yield 1.79 g (93%) of the desired aniline: 1H NMR (400 MHz, CDCl3): δ 8.78 (br d, 1H), 8.21 (dd, 1H), 7.37-7.31 (m, 4H), 7.28-7.24 (m, 1H), 6.44-6.35 (m, 2H), 4.43 (t, 1H), 2.18 (m, 1H), 1.06 (d, 3H), 0.97 (d, 3H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-154412ff41e84ec5b016fa2c74096231
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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