Sodium Methoxide → HCID 59007107, compound

HRID 130410Notes

Reaction equation

HRID 130410 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:14][CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 127613784-Bromo-1-(bromomethyl)-2-nitrobenzene

Product 1

HCID 59007107HCID 59007107, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Bromo-1-(bromomethyl)-2-nitrobenzene (Heterocycles 1994, 39, 767) (8.3 g, 28 mmol) was dissolved in methanol (75 ml) at 0° C. 30% Sodium methoxide in methanol solution (10.7 ml, 56 mmol) was added dropwise and the solution stirred at room temperature for 4 hours. The mixture was concentrated to a small volume and partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and then washed with saturated aqueous sodium bicarbonate solution, water (×3), brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexane to ethyl acetate) to afford the title compound (D16). MS (ES+) m/e 246/248 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to a small volume
  2. custompartitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution, water (×3), brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (hexane to ethyl acetate)

Sources & evidence

ORD record
ord-66e4754fe8fc4a70a51ab6bbcb472323
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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