Methyl iodide → 1-(2-Amino-4-bromophenyl)ethanone

HRID 30310Notes

Reaction equation

HRID 30310 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([CH3:23])=NC(NC(=O)OCC3C=CC=CC=3)C(=O)[NH:10][C:4]=2[CH:3]=1.C(=O)([O-])[O-:27].[K+].[K+].IC>CN(C)C=O.O.C(OCC)(=O)C>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:25]=[CH:24][C:5]=1[C:6](=[O:27])[CH3:23]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135850842HCID 135850842, compound

Product 1

HCID 145036141-(2-Amino-4-bromophenyl)ethanoneYield 148.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

162b (2.0 g, 4.98 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 ml), to this was added potassium carbonate (1.72 g, 12.44 mmol) and iodomethane (0.847 g, 5.97 mmol) and the reaction was sealed in a pressure flask and stirred for 12 hours at room temperature. The reaction was diluted with water and ethyl acetate (20/70 ml). The aqueous solution was then extracted with ethyl acetate (3×20 ml). The organic layers combined, washed with water (1×100 ml), dried over magnesium sulfate, filtered and the filtrate concentrated to give the title compound 162a (1.58 g, 77.596). 1H NMR (CDCl3, 300 MHz): δ 7.43-7.28 (m, 7H), 6.68 (d, 1H, J=8.1 Hz), 5.15-5.05 (m, 3H), 3.38 (s, 3H), 2.45 (d, 3H, 1.5 Hz) ppm.

Workup

  1. customthe reaction was sealed in a pressure flask
  2. extractionThe aqueous solution was then extracted with ethyl acetate (3×20 ml)
  3. washwashed with water (1×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-5208d7607b1d4adf9b53190ffcb81620
Source dataset
uspto-grants-2008_09
Patent number
US07423033B2

Reaction notes

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