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

HRID 2168511Notes

Reaction equation

HRID 2168511 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-09381d35b50b475ea5672713bb5e6f80
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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