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

HRID 8206

Reaction equation

HRID 8206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:13]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 53140362-(Benzyloxy)-1-methoxy-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methoxy-5-nitrophenol (54.3 g, 321 mmol), benzyl bromide (26.5 mL, 223 mmol,) and cesium carbonate (73 g, 223 mmol) is stirred in N,N-dimethylformamide (250 mL) for 24 h at room temperature. The mixture is partitioned between water and ethyl acetate. The layers are separated and the organic layer washed three times with water, once with brine, dried (sodium sulfate), filtered and evaporated to give a crude solid. The crude product is recrystallized from ethyl acetate to yield the title compound, 56.4 g (68%), as a white crystalline solid.

Workup

  1. customThe mixture is partitioned between water and ethyl acetate
  2. customThe layers are separated
  3. washthe organic layer washed three times with water
  4. dry with materialonce with brine, dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude solid
  8. customThe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b0dd637ef9f742f487655199b8f5393a
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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