N-bromobutanimide → 1-(Bromomethyl)-4-methoxy-2-nitrobenzene

HRID 1678709

Reaction equation

HRID 1678709 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 871374-Methyl-3-nitroanisole

Product 1

HCID 37478301-(Bromomethyl)-4-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methyl-3-nitroanisole (2.7 mL; manufactured by Sigma-Aldrich Co.) was dissolved in carbon tetrachloride (20 mL; manufactured by Wako Pure Chemical Industries, Ltd.), and NBS (4.0520 g; manufactured by Tokyo Chemical Industry Co., Ltd.) and hydrated benzoyl peroxide (348 mg; manufactured by Sigma-Aldrich Co.) were added to the solution. The mixture was purged with nitrogen, and was stirred for 3 hours at reflux. The reaction solution was filtered, and then the filtrate was washed with an aqueous solution of NaHSO3 and water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=94:6→73:27). Thus, the title compound (3.2549 g) was obtained.

Workup

  1. customThe mixture was purged with nitrogen
  2. temperatureat reflux
  3. filtrationThe reaction solution was filtered
  4. washthe filtrate was washed with an aqueous solution of NaHSO3 and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=94:6→73:27)

Sources & evidence

ORD record
ord-160003e9764547afa9c7eb3bf7cabab0
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Linked notes

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