Methyl iodide → 1-Bromo-4-methoxy-2-methyl-3-nitrobenzene

HRID 2402697Notes

Reaction equation

HRID 2402697 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 130881794-Bromo-3-methyl-2-nitrophenol

Product 1

HCID 113570121-Bromo-4-methoxy-2-methyl-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-3-methyl-2-nitrophenol (2.200 g, 9.48 mmol) in acetone (35 mL) was added potassium carbonate (3.276 g, 23.70 mmol) and methyl iodide (1.47 mL, 23.70 mmol) and the mixture was heated to reflux for 4 h. The reaction was cooled to rt, filtered and the filtrate was evaporated under reduced pressure to afford the crude product. Purification of the crude product by column chromatography over silica gel eluting with EtOAc/hexane afforded pure 1-bromo-4-methoxy-2-methyl-3-nitrobenzene as pale yellow solid. 1H NMR (400 MHz, CDCl3) δ=2.33 (s, 2H), 3.87 (s, 3H), 6.78 (d, J=8.84 Hz, 1H) and 7.58 (d, J=8.84 Hz, 1H); MS (ES+): m/z 247.26 [MH+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3e2345f247e484abfcb5eb9e9977a21
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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