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

HRID 1910562

Reaction equation

HRID 1910562 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.F[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 167857641-(3-Bromophenyl)ethanamine

Product 1

HCID 58707271N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamineYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(3-bromophenyl)ethanamine (1.0 g, 5.0 mmol), 2,4-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol), N,N-diisopropylethylamine (1.7 mL, 10.0 mmol) and acetonitrile (20 mL) was stirred for 18 h and concentrated in vacuo. The residue was dissolved in ethyl acetate; this solution was washed with water, dried over Na2SO4 and concentrated in vacuo to yield the title compounds as a yellow oil (1.25 g, 74%). 1H NMR (400 MHz, CDCl3): δ 8.51 (d, 1 H), 8.25 (m, 1 H), 7.48 (s, 1 H), 7.41 (m, 1 H), 7.25 (m, 2 H), 6.36 (m, 1 H), 6.24 (m, 1 H), 4.55 (m, 1 H), 1.63 (d, 3 H). MS (ESI) m/z: Calculated: 338; Observed: 339 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthis solution was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1b40f61bab34f9eb067846044c44b58
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Linked notes

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