Benzyl Bromide → 1-(Benzyloxy)-3-nitrobenzene

HRID 2358776Notes

Reaction equation

HRID 2358776 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:11]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 1410991-(Benzyloxy)-3-nitrobenzeneYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Nitro-phenol (1.00 g, 7.189 mmol) was treated with benzyl bromide (1.352 g, 7.91 mmol), and K2CO3 (1.242 g, 8.986 mmol) in DMF. The reaction mixture was heated to 100° C. for 1 hr at which time the reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (1.6 g, 97%).

Workup

  1. temperaturewas cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a5e2c910bc5c4018a56ca33392efa3cf
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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