Benzyl Bromide → 2-(Benzyloxy)-1-methoxy-4-nitrobenzene

HRID 19987

Reaction equation

HRID 19987 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][CH3:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 53140362-(Benzyloxy)-1-methoxy-4-nitrobenzeneYield 96.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (1.65 gm; 12 mmol) was added to a solution of 2-methoxy-5-nitro phenol (1.69 g; 10 mmol) and benzyl bromide (1.71 gm; 10 mmol) in acetone (60 ml). The reaction mixture was refluxed for 12 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (150 ml) and water (50 ml). The ethyl acetate layer was separated, washed with water (2×50 ml), dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 2.5 g of 1-Benzyloxy-2-methoxy-5-nitrobenzene (Yield=96.5%)

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (150 ml) and water (50 ml)
  4. customThe ethyl acetate layer was separated
  5. washwashed with water (2×50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-dfb5a266abc740b7aeafad57481660b5
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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