Benzene, 2-fluoro-4-methyl-1-nitro- → HCID 67422183, compound

HRID 410355Notes

Reaction equation

HRID 410355 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>CCO>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 775714-Bromobenzylamine

Product 1

HCID 67422183HCID 67422183, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-fluoro-4-nitrotoluene (0.30 g, 1.93 mmol) in EtOH (18 ml) at rt under nitrogen was added 4-bromobenzylamine (0.36 g, 1.93 mmol) slowly. The reaction was warmed to reflux where it was maintained for 2 d. After this time, the mixture was cooled to rt and concentrated under reduced pressure. The crude product was partitioned between H2O and EtOAc and the organic phase was separated, washed with 5N HCl, dried (Na2SO4) and concentrated under reduced pressure to provide (4-bromo-benzyl)-(5-methyl-2-nitro-phenyl)-amine (0.45 g, 72%) as a yellow solid.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux where it
  3. temperaturewas maintained for 2 d
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was partitioned between H2O and EtOAc
  6. customthe organic phase was separated
  7. washwashed with 5N HCl
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bfba348adfc4ad0a67cf791ff2cdb05
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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