Benzyl Bromide → HCID 14784149, compound

HRID 447052Notes

Reaction equation

HRID 447052 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O.O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 104889843-Bromo-5-nitrophenol

Product 1

HCID 14784149HCID 14784149, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To an ice-cold solution of 3-bromo-5-nitro-phenol (21.0 g, 96.33 mmol) in acetone (420.0 mL) was added K2CO3 (40.0 g, 289.41 mmol) followed by addition of benzyl bromide (17.20 mL, 144.40 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc (3×250.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified over silica gel (100-200 M, 5% EtOAc-Hexane) to get the desired product (27.0 g, 91%).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (3×250.0 mL)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified over silica gel (100-200 M, 5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-3ff376e1452849618e158cb35421e4a9
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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