Methyl iodide → Methyl 2-amino-5-bromo-3-methylbenzoate

HRID 2369890Notes

Reaction equation

HRID 2369890 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 118503832-Amino-5-bromo-3-methylbenzoic acid

Product 1

HCID 2763413Methyl 2-amino-5-bromo-3-methylbenzoateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-bromo-3-methylbenzoic acid (3.0 g, 13 mmol) from Step A above in DMF was added cesium carbonate (6.4 g, 20 mmol) followed by iodomethane (0.8 ml, 13 mmol). The reaction was stirred at ambient temperature overnight. The mixture was washed with water and extracted with dichloromethane. The organic extract was dried (Na2SO4) and concentrated in vacuo to afford methyl 2-amino-5-bromo-3-methylbenzoate (3.2 g, 100%) as a grey solid: 1H NMR (500 MHz, CDCl3) δ 7.89 (d, J=2.4 Hz, 1H), 7.28 (d, J=2.1 Hz, 1H), 5.84 (brs, 2H), 3.87 (s, 3H), 2.15 (s, 3H); MS (ESI+) m/z 245 (M+H).

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6dc03172bc4d4f0f96da0d728c70f0cf
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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