3-Bromo-2,4,6-trimethylnitrobenzene → HCID 606947, compound

HRID 2105291Notes

Reaction equation

HRID 2105291 reaction equation
Br[C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[C:5]([CH3:12])=[CH:4][C:3]=1[CH3:13].[CH3:14][O-:15].[Na+]>CO.N1C=CC=CC=1>[N+:9]([C:6]1[C:7]([CH3:8])=[C:2]([O:15][CH3:14])[C:3]([CH3:13])=[CH:4][C:5]=1[CH3:12])([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 27572003-Bromo-2,4,6-trimethylnitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 606947HCID 606947, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-bromo-4-nitro-1,3,5-trimethylbenzene (2.0 g, 8.19 mmol) in methanol (20 mL) and pyridine (1.0 mL) under nitrogen was added sodium methoxide (6.2 mL, 32.8 mmol, 30% in methanol), and cuprous chloride (1.62 g, 16.4 mmol). The reaction mixture was heated to 85° C. After 16 hours, it was allowed to cool to room temperature. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate (2×80 mL). The organic phases were combined and washed with saturated aqueous NaCl (2×) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 3-nitro-2,4,6-trimethyl-1-methoxybenzene (0.86 g, 54%) was obtained as a light-yellow liquid.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (2×80 mL)
  4. washwashed with saturated aqueous NaCl (2×)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-53cf208d58e94b8e9f5c11ad33a9d721
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

Loading…