Methyl iodide → (2-Bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine

HRID 1594509Notes

Reaction equation

HRID 1594509 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[Br:15].[H-].[Na+].CI.[C:20]([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[Br:15][C:3]1[CH:4]=[C:5]([C:11]([F:12])([F:13])[F:14])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:1][CH3:20]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1454924-Amino-3-bromo-5-nitrobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 68878922(2-Bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-amino-3-bromo-5-nitrobenzotrifluoride (5.25 g, 18.4 mmol) in DMF (40 mL) was added NaH (883 mg, 60% suspension in mineral oil, 22.1 mmol). After 30 min MeI (1.38 mL, 22.1 mmol) was added. The reaction mixture was allowed to stand at room temperature for 1 h, then was poured into a solution of saturated aqueous NaHCO3 and brine. The resulting suspension was extracted twice with CH2Cl2, and the combined extracts were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (5% EtOAc in hexanes, then 8% EtOAc in hexanes) provided the title compound as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.12 (br s, 1H), 7.86 (d, J=2.0 Hz, 1H), 6.47 (br s, 1H), 3.07 (d, J=5.5 Hz, 3H).

Workup

  1. extractionThe resulting suspension was extracted twice with CH2Cl2
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (5% EtOAc in hexanes

Sources & evidence

ORD record
ord-6b76bf707b20498baf74a6c9e9926e15
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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