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

HRID 1628223Notes

Reaction equation

HRID 1628223 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-nitrophenol 13.A (1.00 g, 4.59 mmol, available from Aldrich) and benzyl bromide (0.55 mL, 5.05 mmol) in DMF (10 mL) was added cesium carbonate (2.2 g, 6.9 mmol). The mixture was stirred overnight at room temperature and then partitioned between AcOEt and water. The organic phase was concentrated to afford 1-((4-bromo-2-nitrophenoxy)methyl)benzene 13.B (1.40 g, 99% yield) which was used in the next step without any further purification.

Workup

  1. custompartitioned between AcOEt and water
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-74931f96a9dd44a6a396dc48260ffafb
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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