Methylamine → 5-Bromo-3-fluoro-N-methyl-2-nitroaniline

HRID 59932

Reaction equation

HRID 59932 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[C:6]([F:14])[C:7]([N+:11]([O-:13])=[O:12])=[C:8](F)[CH:9]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([F:14])[C:7]([N+:11]([O-:13])=[O:12])=[C:8]([NH:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

Product 1

HCID 716520385-Bromo-3-fluoro-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2 M MeNH2 in THF (82 mL) was added dropwise to a solution of 5-bromo-1,3-difluoro-2-nitrobenzene (164 mmol) and Cs2CO3 (197 mmol) in THF (1 L). The reaction mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The two phases were separated and the organic layer was dried (Na2SO4) and concentrated to afford the desired product.

Workup

  1. waitat room temperature for 1 h
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned between EtOAc and H2O
  4. customThe two phases were separated
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dbfc8f0c4dbe4079969af08fe4403998
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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